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Cycloallenes, 11. 1-Phenyl-1,2-cyclononadiene: Preparation and Dimerisation

✍ Scribed by Christl, Manfred ;Moigno, Damien ;Peters, Eva-Maria ;Peters, Karl ;Von Schnering, Hans Georg

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
686 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

1‐Phenyl‐1,2‐cyclononadiene (10) was prepared by addition of dibromocarbene to 1‐phenylcyclooctene and treatment of the resulting 9,9‐dibromobicyclo[6.1.0]nonane 7 with methyllithium. In addition to 10, the 9‐bromo‐9‐methylbicyclononanes cis‐ and trans‐8 as well as the bicyclopropylidene 9 were formed. The dimerisation of 10 proceeded slowly already at room temperature and gave rise to the 1,2‐bismethylenecyclobutane derivatives cis‐ and trans‐11. From the complex mixture that resulted on thermolysis at 200°C of cis‐ and trans‐11 only their isomer 12 could be isolated. Heating of a benzene solution of tetracyanoethylene and cis‐ and trans‐11 afforded the Diels‐Alder adduct 13 of cis‐11, which rearranged to the benzodicyclononene derivative 14 on thermolysis.

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