102070

1,2-propadienyltributylstannane

The reaction of 1,2-propadienyltributylstannane with aldehydes in the presence of TiCl4 at -78°C gives homo-propargylic alcohols in high yields (Scheme 1) (1).

 

A route to the synthesis of chiral propadienyl-carbinols has been described by Corey (Scheme 2) (2).

 

1,2-Propa-dienylstannane reacts with antimony trichloride or tin tetrachloride to afford the corresponding propadienyl compound (Scheme 3) (3).

 

 

References:
(1) J.-I. Haruta, K. Nishi, S. Matsuda, S. Akai, Y. Tamura, Y. Kita J. Org. Chem., 1990, 55, 4853 and M. Suzuki, Y. Morita, R. Noyori J. Org. Chem., 1990, 55, 441.
(2) E. J. Corey, C. M. Yu, D. H. Lee J. Am. Chem. Soc., 1990, 112, 878.
(3) S. Legoupy, L. Lassalle, J.-C. Guillemin, V. Métail; A. Senio, G. Pfister-Guillouzo Inorg. Chem. 1995, 35, 1466.