DIENONE-PHENOL TYPE REARRANGEMENTS .5. CONFIRMATION OF A REARRANGEMENT PATHWAY USING C-13 LABELING

被引：9

作者：

DAVIS, BR

REWCASTLE, GW

WOODGATE, PD

机构：

[1] Department of Chemistry, University of Auckland, Auckland

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1978年 / 07期

关键词：

D O I：

10.1039/p19780000735

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previous work had shown that 2α-hydroxycholest-4-en-3-one (1a) rearranged in acid solution to give the aromatic 2-methoxy-4-methyl-19-norcholesta-1,3,5(10)-triene (2). Labelling of the hydroxy-enone with carbon-13 at C-4 and use of 13C n.m.r. supports previous mechanistic proposals.

引用

页码：735 / 738

页数：4

共 22 条

[1] DIENONE-PHENOL TYPE REARRANGEMENTS .4. 2-HYDROXY-3-OXO-DELTA4-STEROIDS
BAKER, KM
DAVIS, BR
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (22): : 2743 - &
[2] BURN D, 1960, P CHEM SOC LONDON, P14
[3] AROMATIC STEROIDS .3. CHROMIUM TRIOXIDE OXIDATION OF SOME 19-NORCHOLESTA-1,3,5(10)-TRIENES
CAMBIE, RC
CARLISLE, VF
MANNING, TDR
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (09): : 1240 - &
[4] CAMERINO B, 1962, GAZZ CHIM ITAL, V92, P709
[5] SOME REACTIONS OF 2-HYDROXYTESTOSTERONE AND ITS DIACETATE .2.
CLARKE, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (03) : 467 - &
[6] LABILITY OF 6-BROMO-DELTA4-3-OXOSTEROIDS - OBSERVATIONS ON CONVERSION OF 6ALPHA- + 6BETA-BROMOCHOLEST-4-EN-3-1 TO 5ALPHA-CHOLESTANE-3,6-DIONE
COLLINS, DJ
HOBBS, JJ
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (06) : 661 - &
[7] STEROIDAL ALPHA-BETA-EPOXY-KETONES .1. REARRANGEMENT OF 4-ALPHA,5-EPOXY-5-ALPHA-CHOLESTAN-3-ONE AND ITS 4B,5B-ISOMER BY MEANS OF THE BORON TRIFLUORIDE-ETHER COMPLEX
COLLINS, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1959, (DEC): : 3919 - 3928
[8] REARRANGEMENTS OF DELTA-3-2,5-PEROXIDOCHOLESTENE
CONCA, RJ
BERGMANN, W
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (09) : 1104 - 1111
[9] THE STEREOCHEMISTRY OF ALPHA-HALOKETONES .5. PREDICTION OF THE STEREOCHEMISTRY OF ALPHA-BROMINATED KETOSTEROIDS
COREY, EJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (01) : 175 - 179
[10] STEREOELECTRONIC CONTROL IN ENOLIZATION-KETONIZATION REACTIONS
COREY, EJ
SNEEN, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (24) : 6269 - 6278

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