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S-silylmethyl-substituted ketene dithioacetals as synthetic equivalent of a novel 1,3-dipolar reagent, alkylidenethiocarbonyl ylide; synthesis and [3+2] cycloaddition reactions

โœ Scribed by Yoshinori Tominaga; Satoshi Takada; Shinya Kohra

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
312 KB
Volume
35
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Abstmct: 2-(Tr~mcthylsilylmethyNio~~~tI~yltb~o)~t~~yle~~e-i~3-it~an~i~e(l~, readily prepared by reaction of 2-bis(mrrhylrlldo)~~ti:y&ne-~,3-inda~udi~~9) with trirnethylsilylf~t~~yl~~rcaptat~e(l~~, was sltown to be the synthetic equivalent of alkylldene-thiocarbonyl ytide. Treutment of this comporotd with fluvride ions in the presence of reactive hetero-dipol~rophiies such as curbonyl compounds and active alkrms &rdcd I,3+w&r ~~dd~s, 2~~~d~-f,3-~~ola~~es ami 2-ul~iideneth;o~e~ies, by eur~nyZ-s~tj~ted counterparts and ~~'~~tt

~siiylotio~.

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โœ Yoshinori Tominaga; Koichiro Ogata; Shinya Kohra; Makoto Hojo; Akira Hosomi ๐Ÿ“‚ Article ๐Ÿ“… 1991 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 300 KB

## N-(Trrmethylsrlylmethyl)~sothzoureas, readdy prepared by ihe reaction of N-hs(methylthzo)methylenecyanamtde or -p-toluenesulfonamuie wrth (tr~methylstlylmethyl)amme, followed by N-alkylatzon. have been found to be a symhettc equrvalenr of zmznoazomethrne ylrd Treatment of these compounds wzth ces