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Cycloaddition reactions of some 7-alkylidenecycloocta-1,3,5-trienes

✍ Scribed by P.H. Ferber; G.E. Gream; P.K. Kirkbride

Publisher
Elsevier Science
Year
1980
Tongue
French
Weight
181 KB
Volume
21
Category
Article
ISSN
0040-4039

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✦ Synopsis

Novel adducts are formed when 7-methylenecycloocta-1,3,5-triene is treated with reactive dienophiles and chlorosulphonyl isocyanate. Other 7-alkylidenecycloocta-1,3,5trienes form analogous adducts with tetracyanoethylene.

We wish to report that some 7-alkylidenecycloocta-1,3,5-trienes undergo novel cycloaddition reactions. 7-Methylenecycloocta-1,3,5-triene (l)l reacts rapidly with tetracyanoethylene in ethyl acetate to give two adducts, (2) (43%), m.p. 141.5-143', and (3) (11%)3, m.p. 126-127.5". On being warmed, (3) is converted quantitatively into (2). The structure (2) for the major product (designated as the "8 + 2" adduct4) is based on spectral data.5

Likewise, the structure (3) for the minor adduct (designated as the "cyclopropyl" adduct) is also based on spectral data.6 2447

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