Cyclophanes. 8.[2.2](1, 4) Tropylioparacyclophane tetrafluoroborate. Synthesis and charge-transfer interaction

JG O'Connor, PM Keehn

Index: O'Connor,J.G.; Keehn,P.M. Journal of the American Chemical Society, 1976 , vol. 98, p. 8446 - 8450

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Citation Number: 32

Abstract

Abstract: The synthesis of [2.2](1, 4) tropylioparacyclophane tetrafluoroborate (1) is described. It is prepared from [2.2] paracyclophane (4) in six steps in 27% overall yield. Reduction of 4 with N a/NH j affords the tetrahydroderivative tricycle [8.2. 2.24, 7]-hexadeca- 1 (12), 4, 7 (15), lO (l3)-tetraene (5). Treatment of 5 with KO-t-BulCHBr-3 at 0 OC gives a 4.1 mixture of mono-and dicarbene adducts 11, l l-dibromotetracyclo [8.3. 2.24~ 7. O1"~ 12] ...