A highly strained bicyclic allene-bicyclo(3.2.1)octa-2,3-diene intermediate
β Scribed by P. Mohanakrishnan; S.R. Tayal; R. Vaidyanathaswamy; D. Devaprabhakara
- Publisher
- Elsevier Science
- Year
- 1972
- Tongue
- French
- Weight
- 96 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0040-4039
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SUMMA??Y: Treatment of 3-bromo-6,7-benzobicyclo c3.2.11 octa-2,3-diem? (9) with potassium tert.-butoxide produces the strained bicyclic allene (10) which is trapped by 1,3-diphenylbenzo[c]furan (DBI) to give five isomeric cycloadducts. In the absence of DBI, allene (10) gave rise to enol ether ( 18)
8icyclo[3.2.l]octa-3,6-dien-2-ones photoisomerize to ketenes (J + 2; ,4 + 0): When the ketene is hfghly substituted, as in the octamethyl derivative ,$' or is unusually reactive, as in the chloroketene :), intramolecular cycloaddition (GZs + n2a) competes successfully with attack by external nucleop