The Swedish Research Council, the Göran Gustafsson Foundation, COST action 0802 PhoSciNet, and Uppsala University (U3MEC molecular electronics priority initiative) are all acknowledged for financial support.
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Communication
Cascade Reactions Forming Highly Substituted, Conjugated Phospholes and 1,2-Oxaphospholes†
Article first published online: 22 JUN 2012
DOI: 10.1002/anie.201202153
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Arkhypchuk, A. I., Santoni, M.-P. and Ott, S. (2012), Cascade Reactions Forming Highly Substituted, Conjugated Phospholes and 1,2-Oxaphospholes . Angew. Chem. Int. Ed., 51: 7776–7780. doi: 10.1002/anie.201202153
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Publication History
- Issue published online: 25 JUL 2012
- Article first published online: 22 JUN 2012
- Manuscript Revised: 10 MAY 2012
- Manuscript Received: 18 MAR 2012
Funded by
- Swedish Research Council
- Göran Gustafsson Foundation
- Uppsala University
Keywords:
- acetylenes;
- conjugation;
- cumulenes;
- phospha-Wittig;
- reaction mechanisms
More than just a carbon copy: The reaction of a phospha-Wittig–Horner reagent with diacetylenic ketones (see scheme) results in a cascade of reactions that can lead to both an oxaphosphole-terminated cumulene system and an alkene-bridged bis-phosphole. The reaction outcome is determined by the nature of the acetylene termini, with phenyl groups stabilizing a carbene intermediate that dimerizes to give the bis-phosphole product.