REACTIONS OF STEROID HYPOIODIDES .9. CONTRIBUTION TO MECHANISM OF OXIDATIVE CYANOHYDRIN-CYANOKETONE REARRANGEMENT

被引：41
作者：
KALVODA, J
机构：
[1] Chemische Forschungslaboratorien des Departements Pharmazeutika, CIBA AKTIENGESELLSCHAFT, Basel
来源：
HELVETICA CHIMICA ACTA | 1968年 / 51卷 / 02期
关键词：
D O I：
10.1002/hlca.19680510206
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The intramolecular character of the oxidative cyanohydrin‐cyanoketone rearrangement has been proven by cross experiments using 14C‐labeled compounds. The shown stereochemical requirements of the reaction and its analogy to the hypoiodite oxidation [3] of monohydric alcohols lead to the formulation of a reaction mechanism involving an internal addition of a carbon radical centre to the triple bond of a cyano group. Copyright © 1968 Verlag GmbH & Co. KGaA, Weinheim
引用
收藏
页码：267 / &
相关论文
共 21 条
[1]   RADICAL EXCHANGE DURING NITRITE PHOTOLYSIS [J].
AKHTAR, M ;
SAMMES, PG ;
BARTON, DHR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (16) :3394-&
[2]  
AKHTAR M, 1965, J AM CHEM SOC, V87, P460
[3]   OXIDATION OF 1- AND 2-AMINOBENZOTRIAZOLE [J].
CAMPBELL, CD ;
REES, CW .
CHEMICAL COMMUNICATIONS, 1965, (10) :192-&
[4]  
ERCOLI E, 1954, GAZZ CHIM ITAL, V84, P312
[5]   REAKTIONEN VON STEROID-HYPOJODITEN VI SUBSTITUTIONEN TERTIARER WASSERSTOFFATOME .200. [J].
HEUSLER, K ;
KALVODA, J .
HELVETICA CHIMICA ACTA, 1963, 46 (06) :2020-&
[6]   INTRAMOLECULAR FREE-RADICAL REACTIONS [J].
HEUSLER, K ;
KALVODA, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (08) :525-&
[7]  
Heusler K., 1964, ANGEW CHEM, V76, P518
[8]  
JULIA M, 1965, B SOC CHIM FR, P1555
[9]   REAKTIONEN VON STEROID-HYPOJODITEN 8 - 1,4-VERSCHIEBUNG DER NITRILGRUPPE (18-CYANO-PREGNANE) - UBER STEROIDE .206. [J].
KALVODA, J ;
MEYSTRE, C ;
ANNER, G .
HELVETICA CHIMICA ACTA, 1966, 49 :424-&
[10]   INTRAMOLECULAR ORGANOMETAL-ACETYLENE AND ACETYLENE-ACETYLENE INTERACTIONS . ROUTES TO BENZYLIDENEFLUORENE AND C4 RING SYSTEMS [J].
KANDIL, SA ;
DESSY, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (13) :3027-+
123