Add time:09/08/2019 Source:sciencedirect.com
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 reduction. Tetrachlorobenzyne should be considered as an alternative reagent whenever benzyne itself appears to be required.
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