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Thermal and Photochemical Rearrangements of Divinylcyclopropanes to Cycloheptadienes. ‐ A model for the biosynthesis of the cycloheptadiene derivatives found in a seaweed ( Dictyopteris ). Preliminary communication
Author(s) -
Pickenhagen Wilhelm,
Näf Ferdinand,
Ohloff Günther,
Müller Paul,
Perlberger JeanClaude
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560607
Subject(s) - chemistry , biosynthesis , benzene , stereochemistry , irradiation , in vitro , organic chemistry , biochemistry , enzyme , physics , nuclear physics
The activation parameters of the thermal rearrangements of the trans ‐divinylcyclopropanes 1 and 2 , and of cis ‐divinylcyclopropane 3 to give cycloheptadiene 5 have been determined. In addition it has been shown that trans ‐divinylcyclopropane‐cycloheptadiene rearrangements also occur under irradiation by a mercury lamp in benzene at 40°. These low‐temperature in vitro rearrangements suggest that the biosynthesis of the cycloheptadienes in Dictyopteris (dictyopterenes C′ and D′) may proceed by the same reaction(s).