ALICYCLIC COMPOUNDS .3. ACTION OF BASE ON BICYCLIC KETOTOSYLATES - A NOVEL SOLVOLYTIC REARRANGEMENT TO BICYCLO-3-2-0-HEPTENONE DERIVATIVE

被引：12
作者：
MUKHARJI, PC
GANGULY, AN
机构：
[1] Department of Chemistry, Presidency College, Calcutta
来源：
TETRAHEDRON | 1969年 / 25卷 / 21期
关键词：
D O I：
10.1016/0040-4020(69)80049-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The action of KOBut on 10-hydromethyl-Δ3,4-2-octalone tosylate (X) furnished the ketone (XVI) containing a bicyclo[3.2.0]heptanone moiety through solvolytic rearrangement of the homoallylic system. The isomeric 10-hydromethyl-Δ1,9-2-octalone tosylate (XX) however, gave the tricyclic ketone (XXI) without rearrangement.2 2 Presented at the joint annual convention of the Chemical Research Committee of the Council of Scientific and Industrial Research, India and the Society of Biological Chemists (India) at the University of Delhi, December 1966. © 1969.
引用
收藏
页码：5281 / &
相关论文
共 27 条
[1]   A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].
ATTENBURROW, J ;
CAMERON, AFB ;
CHAPMAN, JH ;
EVANS, RM ;
HEMS, BA ;
JANSEN, ABA ;
WALKER, T .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :1094-1111
[2]   STEROIDE UND SEXUALHORMONE .228. ZU SOLVOLYSEVERSUCHEN MIT DELTA4- UND DELTA5-UNGESATTIGTEN 19-MESYLOXY-STEROIDEN [J].
BONET, JJ ;
SCHAFFNER, K ;
WEHRLI, H .
HELVETICA CHIMICA ACTA, 1962, 45 (07) :2615-&
[3]   RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].
BOWDEN, K ;
HEILBRON, IM ;
JONES, ERH ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45
[4]   PHOTOCHEMICAL REACTIONS .9. ISOMERIZATION OF EUCARVONE [J].
BUCHI, G ;
BURGESS, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (16) :4333-4337
[5]   PHOTOCHEMICAL REACTIONS .7. THE INTRAMOLECULAR CYCLIZATION OF CARVONE TO CARVONECAMPHOR [J].
BUCHI, G ;
GOLDMAN, IM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (17) :4741-4748
[6]  
BUCHI G, 1954, J AM CHEM SOC, V76, P353
[7]   PHOTOCHEMICAL TRANSFORMATIONS OF CONJUGATED CYCLOHEPTADIENES [J].
CHAPMAN, OL ;
PASTO, DJ ;
GRISWOLD, AA ;
BORDEN, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (07) :1220-&
[8]   THE ACETOLYSIS OF CIS-9-DECALYLCARBINYL AND TRANS-9-DECALYLCARBINYL PARA-TOLUENESULFONATES [J].
DAUBEN, WG ;
ROGAN, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (18) :5002-5007
[9]   REARRANGEMENT OF 9-HYDROXYMETHYLOCTALIN [J].
HIKINO, Y ;
DEMAYO, P .
CHEMICAL COMMUNICATIONS, 1965, (21) :550-&
[10]   STUDIES IN SESQUITERPENES .22. STRUCTURE OF MUSTAKONE AND COPAENE [J].
KAPADIA, VH ;
NAGASAMP.BA ;
NAIK, VG ;
DEV, S .
TETRAHEDRON, 1965, 21 (03) :607-&
123