Allene formation in reactions of propargyl chlorides with dialkylcuprates and alkylallenylcuprates

DJ Pasto, SK Chou, E Fritzen, RH Shults…

Index: Pasto,D.J. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 1389 - 1394

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Citation Number: 25

Abstract

Dialkylcuprates react with propargyl chlorides to form allenes in generally excellent yield. The mixed n-butylmethyl-and tert-butylmethylcuprates react to preferentially transfer the n- butyl (67: 29) and tert-butyl (97: 3) groups, the latter providing an excellent means for the synthesis of tert-butylallenes. Small amounts of coupled product derived froni the dialkylcuprates are formed, along with allene formally derived by net reduction of the ...