Dehalogenation Reactions by Means of Hexaethylditin. II. : Reactions with gem- or vic-Halides
Hideaki Shirai, Yoshiro Sato, Junichi Tani · YAKUGAKU ZASSHI · 1970
Hexaethylditin (II) reacted with several halomethylbenzenes to give triethyltin halide (V) and the corresponding dimerization products ; 63% bibenzyl (III) from benzyl bromide (Ib), 19.3% trans-stilbene (VIII) from benzal halide (VI), 92.5% cis- and trans-α, α'-dichlorostilbene (XI, XII) from benzotrichloride (IX), and 83.2% tetraphenylethylene (XV) from diphenyldichloromethane (XIV). It has been proved that the stilbene derivatives are formed in this reaction, by way of the dehalogenation reaction of vic-dihalides which were initialy produced as an intermediate. Reaction of DDT (XX) with II, however, mainly afforded DDD (XXI), and trans-p, p'-dichlorostilbene (XXIII) was obtained from the reaction of XXI with II.