4.7 Article

Transition metal-catalyzed synthesis of (E)-2-(Alkylthio)alka-1,3-dienes from allenes and dialkyl disulfides with concomitant hydride transfer

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 345, Issue 5, Pages 560-563

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200303010

Keywords

(E)-2-(alkylthio)alka-1,3-diene; allene; diselenide; disulfide; hydride transfer; rhodium

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Reaction of dialkyl disulfides or diselenides with allenes is catalyzed by a rhodium-phosphine complex and trifluoromethanesulfonic acid giving (E)-2-alkylthio(seleno)-1,3-dienes and (E)-2-alkylthio(seleno)-2-alkenes. Unlike the reaction of alkynes, the reaction of allene is accompanied by hydride transfer.

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