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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 5, Number 1
January 20, 1984 

SN2 Reaction on Silicon-Carbon Bond in the Photoreactions of 2, 3-Benzo-1, 1-diphenyl(or dimethyl)-1-sila-2-cyclobutene with Carbonyl Compounds
Kyung-Tai Kang, Renji Okazaki, Naoki Inamoto
The photoreaction of 2, 3-benzo-1, 1-diphenyl (or dimethyl)-1-sila-2-cyclobutene (9 or 10) with an aldehyde or ketone results in 1:1 cycloadduct of [4 + 2] type. In the reactions of 2, 3-benzo-1, 1-dimethyl-1-sila-2-cyclobutene (10) with acetone and butanone, another 1:1 adducts (13) were also formed, respectively. The following facts indicate that the formation of adduct involves an attack of a triplet carbonyl compound on the silicon of the benzosilacyclobutene, an SH2 process. (1) Even when the reaction of 9 with acetophenone was carried out under conditions such that more than 99% of incident light was absorbed only by acetophenone using the filter solution of aq. cupric sulfate, the same adduct was still formed. (2) When the reaction of 9 with acetone was carried out under oxygen atmosphere, only trace amount of adduct was formed.
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