Addition of sulphenyl halides and thiocyanates to alkenyl-metal compounds. Structures of [1-chloro-2-(4-methyl-2-nitrophenyl)ethyl]-triphenylstannane and [2-(2-nitrophenyl)-1-thiocyanatoethyl]triphenylstannane

Abstract

The crystal and molecular structures of Ph 3SnCHClCH 2SC 6H 3NO 2-2-Y-4 (II, Y  Me) and Ph 3SnCH(SCN)CH 2SC 6H 4NO 2- o (III) have been determined. Compounds II and Ill are adducts of Ph 3SnCHCH 2 and the appropriate sulphenyl chloride and thiocyanate. Both compounds are monomeric and contain slightly distorted tetrahedral tin atoms. The intra-molecular SnS(R) distances in II (Y  Me) and III are 3.67 and 3.58 Å, respectively. The solid state conformations are staggered and have dihedral angles SnCCS of 56.6 and 57.4° in II (Y  Me) and III, respectively, and ClCCS in II and SCCS in III 176.0° and 174.1°, respectively. From 3 J(HH) and 3 J( 119Sn 1H) values, the solid state conformation of II (Y  Me) is calculated to be populated in solution for approximately 1/3rd of the time at 25°C.