Formation of cyclopent[a]indene and acenaphthylene from allyl esters of biphenyl mono- and di-carboxylic acids and from biphenyl dicarboxylic anhydrides on flash vacuum pyrolysis at 1000-1100°C

被引：15

作者：

Bapat, JB ^{[1
]}

Brown, RFC ^{[1
]}

Bulmer, GH ^{[1
]}

Childs, T ^{[1
]}

Coulston, KJ ^{[1
]}

Eastwood, FW ^{[1
]}

Taylor, DK ^{[1
]}

机构：

[1] Monash Univ, Dept Chem, Clayton, Vic 3168, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1997年 / 50卷 / 12期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1071/C97119

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Flash vacuum pyrolysis at 1000-1100 degrees C of the allyl esters of the three isomeric biphenylcarboxylic acids, of the allyl esters of the 12 biphenyldicarboxylic acids and of the three biphenyldicarboxylic anhydrides gave pyrolysates which were examined by H-1 n.m.r. spectroscopy at temperatures below -50 degrees C. In all cases the spectra showed the presence of cyclopent[a]indene and acenaphthylene together with other products. Possible mechanisms for these ring contraction and cyclization processes are discussed and the results of pyrolyses of [2,3-C-13(2)]biphenyl-2,3-dicarboxylic anhydride, and [3,4-C-13(2)]- and (2-H-2(1))-biphenyl-3,4-dicarboxylic anhydrides are reported.

引用

页码：1159 / 1182

页数：24

共 47 条

[1] OBSERVATION OF C-13 REARRANGEMENT IN [C-13(2)]BIPHENYLENE FORMED FROM BENZYNE ON PYROLYSIS OF [1,6-C-13(2)]PHTHALIC ANHYDRIDE AND "[2A,3-C-13(2)]BENZOCYCLOBUTENEDIONE [J].