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Selenothioic acid S-alkyl esters were synthesized from the reaction of terminal acetylenes with n-butyllithium, selenium, and alkanethiols in moderate to high yields. The use of substituted benzene...

Selenothioic acid S -alkyl esters were reacted with allylic bromides in the presence of Et 3 N. Mono-, di- or tri-allylatd products were selectively formed by changing reaction temperatures, times and allylic bromides used. The reaction proceeded with high regio- and stereoselectivity via the seleno-Claisen rearrangement. The selective synthesis of monoallylated esters was also attained by the reaction of in-situ generated lithium eneselenolates with allylic bromides.

The reaction of lithium alkyneselenolates generated from terminal acetylenes with thiols gave rise to lithium eneselenolates with high stereoselectivity. The trapping with alkyl halides afforded ketene selenothioacetals, whereas the trapping with allylic bromides yielded γ,δ-unsaturated selenothioesters via seleno-Claisen rearrangement.

The reaction of lithium alkyneselenolates generated from terminal acetylenes with thiols gave rise to lithium eneselenolates with high stereoselectivity. The trapping with alkyl halides afforded ketene selenothioacetals, whereas the trapping with allylic bromides yielded γ,δ-unsaturated selenothioesters via seleno-Claisen rearrangement.

Selenothioic acid S -alkyl esters were reacted with allylic bromides in the presence of Et 3 N. Mono-, di- or tri-allylatd products were selectively formed by changing reaction temperatures, times and allylic bromides used. The reaction proceeded with high regio- and stereoselectivity via the seleno-Claisen rearrangement. The selective synthesis of monoallylated esters was also attained by the reaction of in-situ generated lithium eneselenolates with allylic bromides.