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First Synthesis of the Dendralene Family of Fundamental Hydrocarbons
Author(s) -
Fielder Simon,
Rowan Daryl D.,
Sherburn Michael S.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001201)39:23<4331::aid-anie4331>3.0.co;2-3
Subject(s) - stille reaction , thermal decomposition , chemistry , organic chemistry , catalysis
A neglected group of highly unsaturated hydrocarbons was how the dendralenes were described 16 years ago in a review in Angewandte Chemie. These compounds are neglected no more! The hitherto unknown [5]‐, [6]‐ (see scheme), and [8]dendralenes are synthesized by thermolysis of masked sulfolene derivatives which, in turn, are prepared by Stille coupling. The same approach offers an improved route to pure samples of [3]‐ and [4]dendralene, the full spectroscopic details of which are reported for the first time.