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HERO ID
5442375
Reference Type
Journal Article
Title
PREPARATION OF 3-METHYLENESILACYCLOBUTANE AND ITS USE IN ORGANIC-SYNTHESIS
Author(s)
Okada, K; Matsumoto, K; Oshima, K; Utimoto, K
Year
1995
Is Peer Reviewed?
1
Journal
Tetrahedron Letters
ISSN:
0040-4039
EISSN:
1873-3581
Volume
36
Issue
44
Page Numbers
8067-8070
DOI
10.1016/0040-4039(95)01710-Y
Web of Science Id
WOS:A1995TB63900032
URL
http://www.sciencedirect.com/science/article/pii/004040399501710Y
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Abstract
Treatment of 3-methylene-1,1-diphenylsilacyclobutane (1a) with dihalo-melhyllithium provided ring expanded 2-halo-4-methylenesilacyclopentane. Heating a mixture of 1a and carbonyl compound such as PhCHO or PhCOMe at reflux in 1,2-dichloroethane afforded 5 methylene 1,1 diphenyl-2-oxa-1-silacyclohexane which was converted into 3-methylene-1,5-alkanediol monomethyl ether upon treatment with dimethyl acelal in the presence of Lewis acid catalyst. Treatment of ketoaldehyde (PhCOCH2CHO) with 1a under BF3· OEt2 catalysis gave 3-methylene-1-phenyl-8 oxabicyclo[3.2.1]octane in one pot
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