Annelated dimethyldihydropyrenes. Electrophilic substitution and valence isomerization to metacyclophanedienes

被引：30

作者：

Mitchell, RH

Iyer, VS

Mahadevan, R

Venugopalan, S

Zhou, PZ

机构：

[1] Department of Chemistry, University of Victoria, Victoria, BC V8W 3P6

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 15期

关键词：

D O I：

10.1021/jo9601573

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reversible valence isomerization of cyclophanedienes to dihydropyrenes is discussed for a number of [a]- and [e]-annelated examples, 5 --> 6 and 7 --> 8, and is related to AM1 and MM2+Pi calculations. Only in [e]-fused systems is the isomerization easily seen to be reversible, Electrophilic substitution of dihydropyrenes is discussed. Nitration of the highly annelated 20 gives a mixture of 8- and 7-nitro derivatives, while NBS/DMF bromination of the benzo[a]dihydropyrene 3 gives mostly la-bromo derivative.

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页码：5116 / 5120

页数：5

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