ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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. 2H- and 13C-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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680427