Unusual Reactions of the 1,3-Dithiane Derivative of the Garner Aldehyde and Related Compounds

Abstract

Treatment of the 1,3-dithiane derivative of the Garner aldehyde with alkyl halides in the presence of n-butyllithium resulted in a ring-opening reaction to give differentially substituted propane-1,3-dithioethers, instead of the expected 2,2-dialkylated 1,3-dithiane products. The corresponding 1,3-dithiolane derivative also reacted in a similar manner. Such ring-opening reactions of dithiane or dithiolane derivatives are rare. A detailed study of this unusual reaction was carried out and a possible mechanism is proposed.

Key words

dithianes - dithiolanes - butyllithium - ring opening - umpolung

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