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Synfacts 2006(1): 0020-0020  
DOI: 10.1055/s-2005-921689
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Acylphospholes

Contributor(s): Victor Snieckus, Oleg M. Demchuk
M. Clochard, J. Grundy, B. Donnadieu, F. Mathey*
University of California Riverside, USA
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Publikationsdatum:
16. Dezember 2005 (online)

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Significance

The first method for the regioselective C3 functionalization of phospholes is presented. The reaction involves a thermal double [1,5] or [1,3] migration of an acyl group and proceeds in low to moderate yields to afford products by potassium tert-butoxide equilibrium displacement. A theoretical rationalization for the migrations is presented.