HYDROGEN PEROXIDE 1
is the hydroperoxide (2) which has been distilled in high vacuum
Hydrogen Peroxide1
ć%
using a bath maintained at 40 C. The hydroperoxide (3) has been
prepared in a similar fashion employing 30% H2O2 (eq 2).12
HOOH
30% H2O2
MeOH, KOH
[7722-84-1] H2O2 (MW 34.02)
rt, 48 h
(2)
t-Bu Br t-Bu OOH
InChI = 1/H2O2/c1-2/h1-2H 42%
InChIKey = MHAJPDPJQMAIIY-UHFFFAOYAL (3)
Tertiary alcohols R1R2R3COH and other alcohols which can
(nucleophilic reagent capable of effecting substitution reactions2
readily furnish carbenium ion intermediates are solvolyzed by
and epoxidation of electron-deficient alkenes;3 weak electrophile
90% H2O2 in the presence of acid catalysts to yield hydroper-
whose activity is enhanced in combination with transition metal
oxides R1R2R3COOH.13 Trimeric hydroperoxides having a nine-
oxides4 and Lewis acids;5 strong nonpolluting oxidant which can
membered oxa heterocyclic ring have been prepared from ketones
oxidize hydrogen halides6)
and hydrogen peroxide in the presence of acid catalysts.14
ć% ć%
N-Alkyl-N -tosyl hydrazides are oxidized by H2O2 and Na2O2
Physical Data: 95% H2O2: mp-0.41 C; bp 150.2 C; d 1.4425
ć% ć% ć%
in THF at rt to the corresponding hydroperoxides; by employing
gcm-3 (at 25 C). 90% H2O2: mp -11.5 C; bp 141.3 C; d
ć% ć%
this procedure, cyclohexyl hydroperoxide has been obtained in
1.3867 g cm-3. 30% H2O2: mp-25.7 C; bp 106.2 C; d 1.108
92% yield.15
gcm-3.
Several gem hydroperoxides have been prepared from acetals
Solubility: sol ethanol, methanol, 1,4-dioxane, acetonitrile, THF,
(eq 3).16
acetic acid.
Form Supplied in: clear colorless liquid widely available as a
OOH
30% H2O2
30% aqueous solution and 50% aqueous solution; 70% and
O O
OOH
THF, H2WO4
90% H2O2 are not widely available.
0 °C, 48 h
(3)
Analysis of Reagent Purity: titration with KMnO4 or cerium(IV)
86%
sulfate.7
Purification: 95% H2O2 (caution!) can be prepared from 50%
The prostaglandin PGG2 (5) has been synthesized from the
solution by distilling off water in a vacuum at rt.8
dibromide (4) (eq 4).17
Handling, Storage, and Precautions: H2O2 having a concen-
CO2H
tration of 50% or more is very hazardous and can explode
Br
violently, particularly in the presence of certain inorganic salts
90% H2O2, Ag+
and easily oxidizable organic material. A safety shield should
be used when handling this reagent.9 After the reaction is
15 20%
Cl
complete, excess H2O2 should be destroyed by treatment with
Br
MnO2 or Na2SO3 soln. Before solvent evaporation, ensure ab-
(4)
sence of peroxides. The use of acetone as solvent should be
CO2H
avoided.10 The reagent should be stored in aluminum drums in
a cool place away from oxidizable substances.
O
(4)
O
OOH
Synthesis of Peroxides via Perhydrolysis. H2O2 and the hy-
(5)
droperoxy anion are excellent nucleophiles which react with alkyl
halides and other substrates having good leaving groups to fur-
Perhydrolysis of acid anhydrides furnishes the corresponding
nish hydroperoxides. The hydroperoxide (2) has been prepared
peroxy acids (for an example, see Trifluoroperacetic Acid). Per-
employing 98% H2O2 (eq 1).11 To a stirred mixture of THF (50
hydrolysis of acid chlorides also furnishes peroxy acids.18 When
mL), Silver(I) Trifluoromethanesulfonate (0.04 mol), and pyri-
an organic acid is mixed with H2O2 an equilibrium reaction is
ć%
dine (0.02 mol) kept at 6 C under argon and protected from light
established, as shown in eq 5.18 Methanesulfonic Acid has been
is gradually added 98% H2O2 (0.32 mol). The chloride (1) (0.02
used to accelerate the reaction and also to function as solvent (see
mol) dissolved in THF (10 mL) is next added dropwise with cool-
preparation of Perbenzoic Acid).
ć%
ing (6 C). The reaction mixture is kept at rt for 24 h; the or-
ganic layer is separated by gravity filtration, diluted with ether,
H+
ć% RCO2H + H2O2 RCO3H + H2O (5)
and washed with saturated aq NaHCO3 at 0 C. The organic layer
is dried. The solvent as well as traces of pyridine and starting ma-
A number of diacyl peroxides have been prepared in 90 95%
terial are distilled out at rt under vacuum. The residual material
yield by reacting the acid chloride (for example, phenylacetyl
Cl H2O2, AgOSO2CF3
OOH chloride) (1 equiv) with 30% H2O2 (0.55 equiv) in ether in the
py, THF
ć%
presence of pyridine (2 equiv) at 0 Cfor 2h.19
rt, 24 h
(1)
83%
Reactions with Amides, Aldehydes, and Ketones. The oxa-
(1) (2) zolidinone (6) is deacylated regioselectively on treatment with
Avoid Skin Contact with All Reagents
2 HYDROGEN PEROXIDE
CO2H CO2H
O O
Lithium Hydroperoxide (eq 6).20 For another example, see
3 3
Evans.21 30% H2O2
MeOH, NaOH
O
(9)
 45 °C, 12 h
30% H2O2
Ph
LiOH, THF, H2O C5H11 C5H11
O OH
rt, 1 h
O O
N
Ph
100% Si(CH2C6H4Me)3 Si(CH2C6H4Me)3
O
(11)
Ä…:² = 94:6
O
(6) Ph
O OH Ä…,²-Unsaturated acids have been epoxidized with 35% H2O2
using a catalyst prepared from 12-tungstophosphoric acid (WPA)
+ NH (6)
HO Ph
ć%
and cetylpyridinium chloride (CPC) (pH 6 7, 60 65 C); by this
O
O method, crotonic acid furnishes the Ä…,²-epoxy acid in 90% yield.29
Synthesis of Epoxides, Vicinal Diols, Dichlorides, and Ke-
Aromatic aldehydes can be transformed to phenols by oxidizing
tones from Alkenes. Terminal alkenes, as well as di- and trisub-
with H2O2 in acidic methanol (eq 7).22 Dilute alkaline H2O2 can
ć%
stituted alkenes, have been epoxidized at 25 C using a molyb-
convert only aldehydes having an hydroxyl in the ortho or para po-
denum blue Bis(tributyltin) Oxide catalyst system (eq 10).30
sition to the corresponding phenols (Dakin reaction).1b m-CPBA
Epoxides have been prepared with 16% H2O2 using a (diperoxo-
is not useful for the preparation of phenol (8) from (7).22
tungsto)phosphate catalyst (12) in a biphasic system.31
60% H2O2
CHO OH
31% H2O2
Mo cat., CHCl3
O
MeOH, KHSO4
O O 3 h
rt, 4 h (10)
(7)
88%
80%
OMe OMe
[(C8H17)3NMe]3+[PO4{W(O)(O2)2}4]3
(7) (8)
(12)
Alkyl and aryl aldehydes are oxidized to the corresponding
Asymmetric epoxidation of 1,2-dihydronaphthalene has been
carboxylic acids in high yields via oxidation with H2O2 in the
achieved employing a chiral manganese(III) salen complex with
presence of Benzeneseleninic Acid as catalyst.23 Cyclobutanones
an axial N-donor; even 1% H2O2 can be used as oxidant and the
and other strained ketones undergo Baeyer Villiger oxidation
highest ee observed was 64%.32
with H2O2. The cyclobutanone (9) has thus been oxidized to the
Vicinal diols have been prepared from alkenes by oxidizing
Å‚-lactone (10) (eq 8).24 Baeyer Villiger oxidation of some cy-
ć%
ć%
clobutanones proceeds under very mild conditions (-78 C).25 with H2O2 in the presence of Re2O7 catalyst, in dioxane at 90 C
for 16 h; the mole ratio of Re2O7:alkene:H2O2 is 1:100:120.
Baeyer Villiger reaction of ketones having isolated double bonds
The reaction proceeds via epoxidation followed by acid-catalyzed
can be carried out with H2O2 without reaction at the double bond;
ring opening. Cyclohexene furnishes trans-cyclohexane-1,2-diol
however, when organic peroxy acids are used, the alkene often is
in 74% yield.33
oxidized.26
Oxidative cleavage of ene lactams takes place during oxida-
tion with H2O2 in the presence of a selenium catalyst (eq 11).34
O
O
The reaction proceeds under neutral and mild conditions. For the
30% H2O2
O
glacial AcOH
preparation of macrocyclic ketoimides, Palladium(II) Acetate is
5 10 °C, 16 h
used as the catalyst.34
(8)
>90%
30% aq H2O2
SeO2, CH2Cl2
HO2C
OMe OMe
(11)
rt, 2 h
(9) (10)
N O O N O
82%
H H
Epoxidation of Ä…,²-Unsaturated Ketones and Acids. Ä…,²- Alkenes have been chlorinated with concentrated HCl/30%
Unsaturated ketones furnish the corresponding Ä…,²-epoxy ketones H2O2/CCl4 in the presence of the phase-transfer catalyst Ben-
in high yields on treatment with H2O2 in the presence of a base.3 zyltriethylammonium Chloride. Side reactions take place when
In the cyclopentenone (11), approach to the ²-face is sterically gaseous chlorine and sulfuryl chloride react with alkenes; under
ć%
hindered. Epoxidation of (11) at -40 C furnishes quantitatively ionic conditions these side reactions are not favored. The method
a 94:6 mixture of Ä…- and ²-epoxides; the selectivity is less when the has also been applied for the bromination of alkenes.6 1-Octene
reaction is carried out at higher temperatures (eq 9).27 Optically furnishes 1,2-dichlorooctane in 56% yield.
active epoxy ketones (about 99%) have been prepared with high ee
by carrying out the epoxidation in the presence of a chiral catalyst Oxidation of Alcohols and Phenols. The system H2O2/
such as polymer-supported poly(L-leucine).28 RuCl3·3H2O/phase-transfer catalyst (didecyldimethylammonium
A list of General Abbreviations appears on the front Endpapers
HYDROGEN PEROXIDE 3
bromide) oxidizes a variety of alcohols selectively; the require- The secondary amine 2-methylpiperidine (13) has been ox-
ment of ruthenium is very low; ratio of substrate:RuCl3 = 625:1.35 idized to the nitrone (14) with H2O2/Na2WO4 (eq 14);45 the
By this method, p-methylbenzyl alcohol was oxidized to p- oxidation product also contains about 6 15% of the isomeric
methyl benzaldehyde in 100% yield. 2-methyl-2,3,4,5-tetrahydropyridine N-oxide (Selenium(IV) Ox-
Vicinal diols are oxidized to Ä…-hydroxy ketones by 35% H2O2 ide is also an effective catalyst for this oxidation).46 1,2,3,4-
in the presence of peroxotungstophosphate (PCWP; 1.6 mol %) Tetrahydroquinoline is oxidized to the 1-hydroxy-3,4-dihydro-
in a biphasic system using CHCl3 as solvent. 1,2-Hexanediol has quinolin-2(1H)-one in 84% yield by H2O2/Na2WO4.47 The flavin,
been oxidized in 93% yield to 1-hydroxy-2-hexanone.36 FlEt+ClO4- (15) is a good catalyst for the H2O2 oxidation of sec-
When 1,4-dihydroxybenzenes are reacted with stoichiomet- ondary amines to nitrones.48
ric quantities of iodine, the corresponding p-benzoquinones are
30% aq H2O2
formed in poor yields; however, they are oxidized in very good
Na2WO4 · 2H2O
yields to p-quinones by reaction with 60% H2O2 in methanol or H2O, add. 30 min
(14)
+
aq solution at rt in the presence of catalytic quantities of I2 or
rt, 3 h
N
N
62 70%
HI. 2-Methyl-1,4-dihydroxynaphthalene has been oxidized to 2-
H
O
methyl-1,4-naphthoquinone in 98% yield.37
(13) (14)
Radical Reactions. Homolytic substitutions of pyrrole, in-
Me
dole, and some pyrrole derivatives have been carried out using
N N O
O
electrophilic carbon centered radicals generated in DMSO by
ClO4
+
+
NMe N
Me
Fe2+/H2O2 and ethyl iodoacetate or related iodo compounds; the
N
substrate is taken in large excess (eq 12).38
Et O t-Bu
(15) (16)
35% H2O2
trans:cis = 95:5
ICH2CO2Et
O O
FeSO4 · 7H2O
DMSO
The tertiary amine N-methylmorpholine has been oxidized to
(12)
ć%
N 90% N
the N-oxide in 84 89% yield; the reaction is carried out at 75 C
Me Me
with 30% H2O2 and the reaction time (0.3 mol scale) is about 24
EtO2C
h.49 The trans-N-oxide (16) has been obtained stereoselectively
(trans:cis = 95:5) by reacting the corresponding N-methylpiperi-
ć%
N-Acylpyrrolidines and -piperidines are oxidized by FeII/
dine with 30% H2O2 in acetone at 25 C.50
hydrogen peroxide in aqueous 95% acetonitrile to the
corresponding pyrrolidin-2-ones and piperidin-2-ones;39 N- Oxidation of Sulfur-containing Compounds. Oxidation of
phenylcarbamoyl-2-phenylpiperidine was oxidized to the corre- di-n-butyl sulfide with H2O2 in the presence of the catalyst
sponding lactam in 61% yield.
FlEt+ClO4- (15) furnished the corresponding sulfoxide in 99%
yield.48 Sulfides have been oxidized to the corresponding sul-
Oxidation of Organoboranes. Oxidative cleavage of the C B
foxides with H2O2 in CH2Cl2 solution in the presence of the
bond with alkaline H2O2 to convert organoboranes to alcohols is
heterocycle (17); di-n-octyl sulfide yields n-octyl sulfoxide in 96%
a standard step in hydroboration reactions. In some procedures,
yield, and benzylpenicillin methyl ester is oxidized to the (S)-S-
organoboranes are formed in the presence of 1,4-oxathiane. When
oxide in 90% yield.51
a mixture of tri-n-octylborane and 1,4-oxathiane in THF was
COMe
treated initially with NaOH and subsequently with 30% H2O2, the
N
organoborane was selectively oxidized to furnish in 98% yield a
N
mixture (93:7) of octan-1-ol and octan-2-ol.40 N
N
(17)
Oxidation of Organosilicon Compounds. Organosilicon
The oxidation of sulfides to sulfones proceeds in good yields
compounds having at least one heteroatom on silicon undergo
when the reaction is catalyzed by tungstic acid; the cyclic sul-
oxidative cleavage of the Si C bond when treated with H2O2
fide thietane is oxidized to the sulfone (thietane 1,1-dioxide) in
(eq 13).41 For additional examples, see Roush42a and Andrey.42b
89 94% yield.52
30% H2O2
KHCO3, KF
OH OH
Oxidation of Selenium-containing Compounds. Oxidation
MeOH, THF
(13)
of the phenyl selenide (18) with H2O2 in THF furnishes the alkene
SiMe2(O-i-Pr) OH
rt, 2 h
77% (19) (eq 15);53 the selenoxide initially formed through oxidation
of (18) undergoes facile syn elimination (see also Grieco54).
SePh
30% H2O2
Oxidation of Amines. H2O2 in the presence of Na2WO4 has
O THF O
O O
been used to oxidize (a) 2,4,4-trimethyl-2-pentanamine to the cor-
25 °C, 12 h
(15)
responding nitroso compound in 52% yield,43 and (b) a primary
90%
amine (containing ²-lactam and phenolic OH) to the correspond-
(18) (19)
ing oxime in 72% yield.44
Avoid Skin Contact with All Reagents
4 HYDROGEN PEROXIDE
Hydrogen peroxide has a high (47%) active oxygen content Related Reagents. Hydrogen Peroxide Ammonium Hepta-
and low molecular weight. It is cheap and is widely available. Af- molybdate; Hydrogen Peroxide Boron Trifluoride; Hydrogen
ter delivering oxygen, the byproduct formed in H2O2 oxidations Peroxide Iron(II) Sulfate; Hydrogen Peroxide Tellurium Dio-
is the nonpolluting water. Hence the use of H2O2 in industry is xide; Hydrogen Peroxide Tungstic Acid; Hydrogen Pero-
highly favored. This reagent is able to oxidize SeO2, WO3, MoO3, xide Urea; Iron(III) Acetylacetonate Hydrogen Peroxide; Per-
and several other inorganic oxides efficiently to the correspond- benzoic Acid; Peroxyacetimidic Acid; Trifluoroperacetic Acid.
ing inorganic peroxy acids which are the actual oxidizing agents
in many reactions described above.4 Use of these oxides in cat-
alytic amounts along with H2O2 as the primary oxidant reduces
1. (a) Kirk-Othmer Encyclopedia of Chemical Technology; Wiley: New
the cost of production, simplifies workup and minimizes the efflu-
York, 1978; Vol. 3, p 944; Vol. 13 p 12; Vol. 2, p 264. (b) Fieser, L. F.;
ent disposal problem. Phase-transfer-catalyzed (PTC) reactions in
Fieser, M., Fieser & Fieser 1967, 1, 456.
a two-phase system are well suited for H2O2 oxidations and are
2. Swern, D. In Comprehensive Organic Chemistry; Barton, D. H. R., Ed.;
widely used; epoxides are susceptible to ring opening by water
Pergamon: Oxford, 1979; Vol. 1. p 909.
and the PTC procedure allows the preparation of epoxides even
3. Weitz, E.; Scheffer, A., Chem. Ber. 1921, 54, 2327.
with 16% aq H2O2 since the epoxide and water are in different
4. Mimoun, H. In Comprehensive Coordination Chemistry; Wilkinson, G.,
phases.31 Handling chlorine and bromine poses many problems,
Ed., Pergamon: Oxford, 1987, Vol. 6, p 317.
but HCl/H2O2 and HBr/H2O2 systems may be used as substi-
5. Olah, G. A.; Fung, A. P.; Keumi, T., J. Org. Chem. 1981, 46, 4305.
tutes for chlorine and bromine, respectively.6 The solids Sodium
6. Ho, T.-L.; Gupta, B. G. B.; Olah, G. A., Synthesis 1977, 676.
Perborate, sodium percarbonate, and Hydrogen Peroxide Urea,
7. Swern, D. Organic Peroxides; Wiley: New York, 1970; Vol. 1, p 475.
which are prepared from H2O2, have wide applications since they
8. Cofre, P.; Sawyer, D. T., Inorg. Chem. 1986, 25, 2089.
release H2O2 readily.
9. (a) Pagano, A. S.; Emmons, W. D., Org. Synth. 1969, 49, 47.
(b) Hazards in the Chemical Laboratory; Luxon, S. G., Ed.; Royal
Reactions with Nitriles. Treatment of nitriles (20) with
Society of Chemistry: Cambridge, 1992.
NaOH/H2O2 in aqueous ethanol is a standard synthetic proce-
10. Organic Peroxides; Swern, D., Ed.; Wiley: New York, 1970; Vol. 1, p 1.
dure for the preparation of amides (21); aromatic nitriles furnish
11. Frimer, A. A., J. Org. Chem. 1977, 42, 3194.
amides in high yields but aliphatic nitriles give amides in moder-
12. Bloodworth, A. J.; Curtis, R. J.; Spencer, M. D.; Tallant, N. A.,
ate yields (50 60%).55 It has been suggested56 that addition of the
Tetrahedron 1993, 49, 2729.
hydroperoxy anion to the nitrile (20) furnishes the peroxycarbox-
13. Davies, A. G.; Foster, R. V.; White, A. M., J. Chem. Soc. 1953, 1541.
imidic acid (22) which reacts with H2O2 to give the amide (21)
14. Story, P. R.; Lee, B.; Bishop, C. E.; Denson, D. D.; Busch, P., J. Org.
and molecular oxygen.
Chem. 1970, 35, 3059.
15. Caglioti, L.; Gasparrini, F.; Palmieri, G., Tetrahedron Lett. 1976, 3987.
O NH
16. Jefford, C. W.; Li, Y.; Jaber, A.; Boukouvalas, J., Synth. Commun. 1990,
R NR R
20, 2589.
NH2 OOH
17. Porter, N. A.; Byers, J. D.; Ali, A. E.; Eling, T. E., J. Am. Chem. Soc.
(20) (21) (22)
1980, 102, 1183.
18. Ogata, Y.; Sawaki, Y., Tetrahedron 1967, 23, 3327.
It has been observed57 that in the reaction of nitriles with 30%
19. Kochi, J. K.; Macadlo, P. E., J. Org. Chem. 1965, 30, 1134.
H2O2 in the presence of 20% NaOH there is a significant increase
20. (a) Gage, J. R.; Evans, D. A., Org. Synth. 1990, 68, 83. (b) Evans, D. A.;
in the reaction rate when n-tetrabutylammonium hydrogen sulfate
Britton, T. C.; Ellman, J. A., Tetrahedron Lett. 1987, 28, 6141.
(20 mol %) is used as phase-transfer catalyst. The reaction is car-
21. Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L., J. Am. Chem.
ć%
ried out at 25 C for 1 2 h employing CH2Cl2; aromatic as well
Soc. 1990, 112, 4011.
as aliphatic amides are obtained in high yields (e.g. eq 16). This
22. Matsumoto, M.; Kobayashi, H.; Hotta, Y., J. Org. Chem. 1984, 49, 4740.
method cannot be used if the nitrile has an electron-withdrawing
23. Choi, J.-K.; Chang, Y.-K.; Hong, S. Y., Tetrahedron Lett. 1988, 29, 1967.
substituent on the carbon atom Ä… to the cyano group.57
24. Corey, E. J.; Arnold, Z.; Hutton, J., Tetrahedron Lett. 1970, 307.
25. Crimmins, M. T.; Jung, D. K.; Gray, J. L., J. Am. Chem. Soc. 1993, 115,
CN CONH2 3146.
1.6 h
(16)
26. Feldman, K. S.; Wu, M.-J.; Rotella, D. P., J. Am. Chem. Soc. 1990, 112,
97%
8490.
27. Corey, E. J.; Ensley, H. E., J. Org. Chem. 1973, 38, 3187.
Treating a DMSO solution of a nitrile with an excess of 30%
28. Itsuno, S.; Sakakura, M.; Ito, K., J. Org. Chem. 1990, 55, 6047.
H2O2 in the presence of a catalytic amount of K2CO3 for 1 30 min
29. Oguchi, T.; Sakata, Y.; Takeuchi, N.; Kaneda, K.; Ishii, Y.; Ogawa, M.,
ć%
at 25 C furnishes the corresponding amide in high yields58 (e.g.
Chem. Lett. 1989, 2053.
eq 17). Under these conditions, esters, amides, and urethanes do
30. Kamiyama, T.; Inoue, M.; Kashiwagi, H.; Enomoto, S., Bull. Chem. Soc.
not react. Ä…,²-Unsaturated nitriles furnish Ä…,²-epoxy amides.58
Jpn. 1990, 63, 1559.
For other routes for the synthesis of amides from nitriles, see
31. Venturello, C.; D Aloisio, R., J. Org. Chem. 1988, 53, 1553.
Cacchi57 and Katritzky.58
32. Schwenkreis, T.; Berkessel, A., Tetrahedron Lett. 1993, 34, 4785.
33. Warwel, S.; Rusch gen, ; Klaas, M.; Sojka, M., J. Chem. Soc., Chem.
30% H2O2
DMSO, K2CO3 Commun. 1991, 1578.
20 °C, 5 min
34. Naota, T.; Sasao, S.; Tanaka, K.; Yamamoto, H.; Murahashi, S.-I.,
Cl (17)
CN Cl CONH2
85%
Tetrahedron Lett. 1993, 34, 4843.
A list of General Abbreviations appears on the front Endpapers
HYDROGEN PEROXIDE 5
35. Barak, G.; Dakka, J.; Sasson, Y., J. Org. Chem. 1988, 53, 3553. 48. Murahashi, S. I.; Oda, T.; Masui, Y., J. Am. Chem. Soc. 1989, 111,
5002.
36. Sakata, Y.; Ishii, Y., J. Org. Chem. 1991, 56, 6233.
49. VanRheenen, V.; Cha, D. Y.; Hartley, W. M., Org. Synth. 1978,
37. Minisci, F.; Citterio, A.; Vismara, E.; Fontana, F.; Bernardinis, S. D., J.
58, 44.
Org. Chem. 1989, 54, 728.
50. Shvo, Y.; Kaufman, E. D., J. Org. Chem. 1981, 46, 2148.
38. Baciocchi, E.; Muraglia, E.; Sleiter, G., J. Org. Chem. 1992, 57, 6817.
51. Torrini, I.; Paradisi, M. P.; Zecchini, G. P.; Agrosi, F., Synth. Commun.
39. Murata, S.; Miura, M.; Nomura, M., J. Chem. Soc., Perkin Trans. 1 1987,
1987, 17, 515.
1259.
52. Sedergran, T. C.; Dittmer, D. C., Org. Synth. 1984, 62, 210.
40. Brown, H. C.; Mandal, A. K., J. Org. Chem. 1980, 45, 916.
53. Jones, G. B.; Huber, R. S.; Chau, S., Tetrahedron 1993, 49, 369.
41. Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M., Org. Synth. 1990, 69, 96and
references cited therein. 54. Grieco, P. A.; Yokoyama, Y.; Gilman, S.; Nishizawa, M., J. Org. Chem.
1977, 42, 2034.
42. (a) Roush, W. R.; Grover, P. T., Tetrahedron 1992, 48, 1981. (b) Andrey,
O.; Landais, Y.; Planchenault, D., Tetrahedron Lett. 1993, 34, 2927. 55. Noller, C. R., Org. Synth., Coll. Vol. 1943, 2, 586.
43. Corey, E. J.; Gross, A. W., Org. Synth. 1987, 65, 166. 56. Wiberg, K., J. Am. Chem. Soc. 1953, 75, 3961.
44. Salituro, G. M.; Townsend, C. A., J. Am. Chem. Soc. 1990, 112, 760. 57. Cacchi, S.; Misiti, D.; La Torre, F., Synthesis 1980, 243.
45. Murahashi, S.-I.; Shiota, T.; Imada, Y., Org. Synth. 1992, 70, 265. 58. Katritzky, A. R.; Pilarski, B.; Urogdi, L., Synthesis 1989, 949.
46. Murahashi, S.-I.; Shiota, T., Tetrahedron Lett. 1987, 28, 2383.
47. Murahashi, S.-I.; Oda, T.; Sugahara, T.; Masui, Y., J. Org. Chem. 1990, A. Somasekar Rao & H. Rama Mohan
55, 1744.
Indian Institute of Chemical Technology, Hyderabad, India
Avoid Skin Contact with All Reagents