Cyclopropylidene rearrangement in the reduction of 1, 2: 3, 4-bis (dihalomethano)-1, 2, 3, 4-tetrahydropolymethylnaphthalenes by naphthalenides

…, K Harada, T Yagi, Y Shirahase

Index: Oku, Akira; Harada, Ken; Yagi, Tohru; Shirahase, Yasushi Journal of the American Chemical Society, 1983 , vol. 105, # 13 p. 4400 - 4407

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Citation Number: 9

Abstract

Abstract: The reduction of octamethyl-substituted title compound (la) with Na naphthalene in THF at-70" C afforded 1, 2: 3, 4-diethylideno-1, 2, 3, 4-tetrahydro-2, 3, 5, 6, 7, 8- hexamethylnaphthalene (2a, 75%), whereas at 25 OC a mixture of 1, 2, 3, 4, 5, 7, 8, 9- octamethylbenzocycIooctene (Sa) and 2, 3, 5, 6, 7, 8, 9-heptamethyI-1-ethylideno-1H- benzocycloheptene (4a) but not 2a was formed. The structure of Za was determined by its ...

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