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Synthesis and a [π2s+ π2s+ π2s] cycloaddition reaction of 5,8-dimethylene-1,3,6-cyclooctatriene

✍ Scribed by Masaji Oda; Nobuyuki Fukazawa; Yoshio Kitahara

Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
238 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis

Dimethylenecyclopolyenes of type 1. are an interesting class of compounds.

The n=l member of this class is 3,6-dimethylene-1,4-cyclohexadiene 2 which is an important intermediate for [2.2]paracyclophane.

1 -Of two possible dimethylenecyclooctatrienes, 7,8-dimethylene-1,3,5-cyclooctatriene 2 was synthesized as a substantially reactive substance. 2 As to 5,8-dimethylene-1,3,6-cyclooctatriene 4_, we have reported the synthesis of the tetraphenyl derivative 2 by thermal ring opening of its valence isomer.

3 We wish here to report the synthesis of the parent compound 4 by a similar strategy and its cycloaddition reaction with -N-phenyltriazolinedione. 7) This ca 1:l mixture was obtained when the pyrolysis was done at 350°C.

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