PYROTHIOCARBONATES V. SYNTHESIS AND SOME REACTIONS OF S-TRIMETHYLSILYL O-ALKYLDITHIOCARBONATES

Abstract

Non-reported S-trimethylsilyl O-alkyldithiocarbonates (2) are prepared by reaction of O,O-dialkyltrithiodicarbonates with N-methyl N-trimethylsilylaniline in 87-96% yield. These are air-sensitive liquids which are separated from the accompanying phenyl methyl alkylcarbamothioates by fractional distillation. The reaction of 2 with acetyl chloride gives the unsymmetrical dithioanhydrides S-acetyl Oalkyldithiocarbonates in 93-97% yield. With the less powerful electrophilic reagent, iodomethane, Strimethylsilyl O-ethyldithiocarbonate (2a) forms S-methyl O-ethyldithiocarbonate in 30% yield. When a chloroform solution of 2a is stirred with water the unstable compound O-ethyldithiocarbonic acid is obtained.

Key Words:

• Masked O-alkyldithiocarbonic acids
• O,O-dialkyltrithiodicarbonates
• S-acetyl O-alkyldithiocarbonates.