The Dechlorination of Some Highly Chlorinated Naphthalene Derivatives
The 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 reduction.Tetrachlorobenzyne should be considered as an alternative reagent whenever benzyne itself appears to be required.
Hales, Neil J.,Heaney, Harry,Hollinshead, John H.,Lai, Steven M. F.,Singh, Pritpal
p. 7777 - 7790
(2007/10/02)
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