OXIDATIONS BY METHYL(TRIFLUOROMETHYL)DIOXIRANE .2. SELECTIVE POLYOXYFUNCTIONALIZATION OF ADAMANTANE

被引：68

作者：

MELLO, R ^{[1
]}

CASSIDEI, L ^{[1
]}

FIORENTINO, M ^{[1
]}

FUSCO, C ^{[1
]}

CURCI, R ^{[1
]}

机构：

[1] UNIV BARI,DEPARTIMENTO CHIM,CTR CNR MISO,VIA AMENDOLA 173,I-70126 BARI,ITALY

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)89027-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Adamantane (1) can be converted directly into adamantan-1,3,5-triol (5) and into adamantan-1,3,5,7-tetraol (6) under remarkably mild conditions by employing an excess of isolated methyl(trifluoromethyl)dioxirane (3a) in solution. This new dioxirane species was found to be over 7,000-fold more reactive than dimethyldioxirane (3b) in performing adamantane hydroxylations. © 1990.

引用

页码：3067 / 3070

页数：4

共 36 条

[1] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].

ADAM, W ;

CHAN, YY ;

CREMER, D ;

GAUSS, J ;

SCHEUTZOW, D ;

SCHINDLER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803

[2] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[3] FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .14. FURTHER-STUDIES ON THE MECHANISM OF GIF-TYPE SYSTEMS [J].

BARTON, DHR ;

HALLEY, F ;

OZBALIK, N ;

SCHMITT, M ;

YOUNG, E ;

BALAVOINE, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7144-7149

[4] DIMETHYLDIOXIRANE - MECHANISM OF BENZALDEHYDE OXIDATION [J].

BAUMSTARK, AL ;

BEESON, M ;

VASQUEZ, PC .

TETRAHEDRON LETTERS, 1989, 30 (41) :5567-5570

[5] CATALYTIC HOMOGENEOUS FUNCTIONALIZATION OF ADAMANTANE - INFLUENCE OF ELECTRONIC AND STRUCTURAL FEATURES OF THE METALLOPORPHYRIN CATALYST ON ATOM TRANSFER SELECTIVITY (OXYGENATION VERSUS AZIDIFICATION HALOGENATION) [J].

BROWN, RB ;

HILL, CL .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5762-5768

[6] O-17 AND C-13 IDENTIFICATION OF THE DIMETHYLDIOXIRANE INTERMEDIATE ARISING IN THE REACTION OF POTASSIUM CARBONATE WITH ACETONE [J].

CASSIDEI, L ;

FIORENTINO, M ;

MELLO, R ;

SCIACOVELLI, O ;

CURCI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :699-700

[7]

CICALA G, 1982, J ORG CHEM, V47, P2679

[8] DRY OZONATION - METHOD FOR STEREOSELECTIVE HYDROXYLATION OF SATURATED COMPOUNDS ON SILICA-GEL [J].

COHEN, Z ;

KEINAN, E ;

MAZUR, Y ;

VARKONY, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (14) :2141-2142

[9] ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED ALKENES BY DIOXIRANE INTERMEDIATES GENERATED FROM POTASSIUM PEROXOMONOSULPHATE AND CHIRAL KETONES [J].

CURCI, R ;

FIORENTINO, M ;

SERIO, MR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) :155-156

[10]

CURCI R, 1980, J ORG CHEM, V45, P475

← 1 2 3 4 →