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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 13, Number 1
BKCSDE 13(1)
January 20, 1992 

 
Title
Regioselectivity in the Cycloaddition Reactions of t-Butyl Trimethylsilyl Thioketone with 1,3-Butadienes
Author
Kyung-Tae Kang*, Chi Hyo Park, Ung Chan Yoon
Keywords
Abstract
Thermal cycloaddition of t-butyl trimethylsilyl thioketone (1) with 2-substituted dienes such as isoprene and 2-trimethylsilyloxy-1,3-butadiene occurred smoothly at 80℃ to afford regioiomeric mixtures of cycloadducts. On the other hand, similar treatment of 1 with 1-substituted dienes such as trans-1,3-pentadiene, 1-methoxy-and 1-acetoxy-1,3-butadiene and Danishefsky's diene afforded a single regioisomeric adduct, respectively. Protodesilylation of the silylated adducts 8 and 11 could also be performed with ease.
Page
41 - 45
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