Trapping of 1,2-benzo-1,3,4-cycloheptatriene as evidence for a strained cyclic allene structure

1999-07-23
Yildiz, YK
Ozturk, T
Balcı, Metin
8-brom-6,7-dihydrobenzocycloheptene 16 and 9-bromo-6,7-benzocycloheptadiene 17 have been synthesized via a new and simple method, and their allene reactions were studied. Treatment of 16 with a base in the presence of DPIBF (diphenylisobenzofuran) gave the strained bicyclic allene 9, which underwent a cycloaddition reaction to yield 25 and 26. On the other hand, the reaction of the vinyl bromide 17 with a base, either in the presence or absence of DPIBF, resulted in the formation of 7H-benzocycloheptadiene 21, rather than the alkyne 22.

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Citation Formats
Y. Yildiz, T. Ozturk, and M. Balcı, “Trapping of 1,2-benzo-1,3,4-cycloheptatriene as evidence for a strained cyclic allene structure,” TETRAHEDRON, pp. 9317–9324, 1999, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56530.