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

收藏

页码：735 / 738

页数：4

相关论文

共 22 条

[1] DIENONE-PHENOL TYPE REARRANGEMENTS .4. 2-HYDROXY-3-OXO-DELTA4-STEROIDS [J].

BAKER, KM ;

DAVIS, BR .

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 [J].

CAMBIE, RC ;

CARLISLE, VF ;

MANNING, TDR .

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. [J].

CLARKE, RL .

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 [J].

COLLINS, DJ ;

HOBBS, JJ .

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 [J].

COLLINS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (DEC) :3919-3928

[8] REARRANGEMENTS OF DELTA-3-2,5-PEROXIDOCHOLESTENE [J].

CONCA, RJ ;

BERGMANN, W .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (09) :1104-1111

[9] THE STEREOCHEMISTRY OF ALPHA-HALOKETONES .5. PREDICTION OF THE STEREOCHEMISTRY OF ALPHA-BROMINATED KETOSTEROIDS [J].

COREY, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (01) :175-179

[10] STEREOELECTRONIC CONTROL IN ENOLIZATION-KETONIZATION REACTIONS [J].

COREY, EJ ;

SNEEN, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (24) :6269-6278