ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
It is shown that dimethyl 5, 6, 8, 10-tetramethyl- (3) and 8- (tert-butyl)-5,6,10-trimethylheptalene-1, 2-dicarboxylate (5), and their derivatives rearrange reversibly on irradiation or on heating to yield the corresponding 1,6,8,10-tetramethyl- (4) and 8-(tert-butyl)-1,6,10-trimethylheptalene-1,2-dicarboxylate (6), and their derivatives by double-bond shift (π-skeletal rearrangement) via a transition state with D2 symmetry as the highest possible one. This follows from the fact that (-)-(P)-3 is photochemically as well as thermally rearranged to give (-)-(P)-4 i.e. the π-skeletal rearrangement occurs with retention of configuration of the heptalene skeleton and without loss of optical purity.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680216