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σ-Skeletal-Rearrangement of Heptalenes: Thermal Transformation of Heptalene-1,2-dicarboxylates into Heptalene-1,3-dicarboxylates

✍ Scribed by Werner Bernhard; Paul Brügger; John J. Daly; Gerhard Englert; Peter Schönholzer; Hans-Jürgen Hansen

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
968 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

It is shown that dimethyl heptalene‐1,2‐dicarboxylates undergo rearrangements at temperatures > 200° to yield the corresponding 1,3‐dicarboxylates, which are isolated as the more stable 3,5‐dicarboxylates. ^2^H‐ and ^13^C‐labelling experiments with dimethyl 7‐isopropyl‐5,10‐dimethylheptalene‐1,2‐dicarboxylate (1) which is rearranged into dimethyl 9‐isopropyl‐1,6‐dimethylheptalene‐3,5‐dicarboxylates. (2) indicate that the reaction occurs by interchange of C(2) and C(3) in the heptalene skeleton of 1. Thus, the transformation of 1 into 2 represents the first thermal σ‐skeletal rearrangement of heptalenes. The structures of 1 and 2 are discussed in terms of an X‐ray analysis and the spectral data.

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