CYCLOBUTENE DERIVATIVES AS ISOPRENE EQUIVALENTS IN TERPENE SYNTHESIS .3. BICYCLO[2.2.0]HEXANES

被引：49

作者：

WILSON, SR ^{[1
]}

PHILLIPS, LR ^{[1
]}

PELISTER, Y ^{[1
]}

HUFFMAN, JC ^{[1
]}

机构：

[1] INDIANA UNIV,CTR MOLEC STRUCT,BLOOMINGTON,IN 47401

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 24期

关键词：

D O I：

10.1021/ja00518a040

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two new syntheses of cyclobutene esters and the use of 1-cyanocyclobutene as potential isoprene synthons are described. Photocycloaddition of methyl cyclobut-1-enecarboxylate and 1-cyanocyclobutene to piperitone, followed by reduction and lactonization, gives photodihydroaristolactone 15. Single-crystal X-ray analysis of 15 and related 4 reveals interesting structural features in the strained bicyclo[2.2.0]hexane system. Thermolysis of lactones 15 and 4 yields 1,5-cyclodecadienes related to germacrene sesquiterpenes. © 1979, American Chemical Society. All rights reserved.

引用

页码：7373 / 7379

页数：7

共 57 条

[1] AN ELECTRON DIFFRACTION INVESTIGATION OF MOLECULAR STRUCTURE OF ANTI-TRICYCLO(4.2.0.02,5)OCTANE AND SYN-TRICYCLO(4.2.0.02,5)OCTANE IN VAPOUR PHASE [J].