Journal of the American Chemical Society

Carbenes from Derivatives of Ethynylcarbinols. The Synthesis of Alkenylidenecyclopropanes1

HD Hartzler

Index: Hartzler,H.D. Journal of the American Chemical Society, 1961 , vol. 83, p. 4990 - 4996

Full Text: HTML

Citation Number: 73

Abstract

Ethynyldialkylcarbinyl chlorides undergo very slow solvolysis in aqueous ethanol at room temperature."-'In acidic solution, isomerization of the chlorides to chloroallenes can occur. J In the presence of base, these tertiary acetylenic halides undergo a replacement reaction which is kinetically of second~ rder.~.~ J The products are the unrearranged tertiary acetylenic ethers. Since a bimolecular displacement on the tertiary halide appears highly ...