Tetrahedron

The dechlorination of some highly chlorinated naphthalene derivatives

NJ Hales, H Heaney, JH Hollinshead, SM Lai, P Singh

Index: Hales, Neil J.; Heaney, Harry; Hollinshead, John H.; Lai, Steven M. F.; Singh, Pritpal Tetrahedron, 1995 , vol. 51, # 28 p. 7777 - 7790

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Citation Number: 9

Abstract

The [4+ 2] cycloadducts formed between tetrachlorobenzyne and a variety of arenes and cyclic 1, 3-dienes have been reductively dechlorinated. The products are formally benzyne cycloadducts, many of which are difficult to make by other routes. High yields are obtained when sodium and t-butanol in boiling THF are used for the reduction. THF serves as a solvent but t-butanol not only acts as a proton donor but also appears to initiate the ...

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