1-CHLORO-1-METHYLSILACYCLOBUTANE

Physical properties

bp 103°C; d 0.985 g cm?3.

The Uses of 1-CHLORO-1-METHYLSILACYCLOBUTANE

Siletanes (silacyclobutanes) represent a unique class of silicon-based reagents that have enjoyed much success in a number of synthetic applications including aldol reactions, allylations, cross-coupling reactions, carbosilane oxidations, and ring expansions. The manifestation of their strain in enhanced Lewis acidity and in the ring opening to silanols accounts for their utility. 1-Chloro-1-methylsiletane can be used for the preparation of the various siletane derivatives for these applications.
Grignard reagents react efficiently with 1-chloro-1-methylsiletane to provide the corresponding aryl-, alkenyl-, or alkylsiletanes (eqs 1–3).On the contrary, reactions with alkyllithiums are limited to the reaction of 1 with a lithium acetylide (eq 4).The reaction of 1 with an intermediate vinylalane obtained by hydroalumination of 1-heptyne gave (E)-1-heptenylmethylsiletane in >99/1 isomeric purity (eq 5).The reaction of 1 with LiAlD4 afforded 1-deuterio-1-methylsiletane (eq 6).

The Uses of 1-CHLORO-1-METHYLSILACYCLOBUTANE

Intermediate in the formation of enoxysilacyclobutanes.

Preparation

siletane can be prepared in large quantities byWurtz coupling reaction of dichloro-3-chloropropylmethylsilane with Mg.It is commercially available from Gelest and Aldrich chemical company.