Carbonyl Allenylations andPropargylations by 3-Chloro-1-propyne or 2-Propynyl Mesylateswith Tin(IV) Chloride and Tetrabutylammonium Iodide

Abstract By the use of tin(IV) chloride and tetrabutylammonium iodidein dichloromethane, 3-chloro-1-propyne or 2-propynyl mesylate canbe applied to allenylation and propargylation of aldehydes (carbonylallenylation and propargylation) to produce a mixture of 1-substituted2,3-butadien-1-ols and 1-substituted 3-butyn-1-ols. 1-Substituted2-propynyl mesylates selectively cause carbonyl propargylation,while 3-substituted 2-propynyl mesylates cause carbonyl allenylation.