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C, C-Diacetylenic Phosphaalkenes as Heavy Diethynylethene Analogues
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2009 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 74, no 24, 9265-9273 p.Article in journal (Refereed) Published
Abstract [en]

A series of C,C-diacetylenic phosphaalkenes 1be has been prepared from 1-chloropenta-1,2-dien-4-ynes 6be in a reaction with Mes*PCl2 (Mes* = 2,4,6-(tBu)3Ph) in the presence of LDA. Under identical conditions, isomeric butadiyne-substituted phosphaalkenes 2cf can be obtained from 3-chloropenta-1,4-diynes 5cf. The title compounds represent rare examples of diethynylethenes in which a constituting methylene has been replaced by a phosphorus center. The formation of both isomers can be rationalized by a common pathway that involves isomeric allenyllithium species. Spectroscopic, electrochemical, and theoretical investigations show that the phosphorus heteroatoms are an intrinsic part of the compounds’ π−systems and lead to decreased HOMO−LUMO gaps compared to those in all-carbon-based reference compounds.

Place, publisher, year, edition, pages
2009. Vol. 74, no 24, 9265-9273 p.
National Category
Inorganic Chemistry
Research subject
Inorganic Chemistry
URN: urn:nbn:se:su:diva-35521DOI: 10.1021/jo901942uISI: 000272462100002OAI: diva2:288955
Available from: 2010-01-22 Created: 2010-01-18 Last updated: 2011-05-17Bibliographically approved

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Kritikos, Mikael
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Department of Physical, Inorganic and Structural Chemistry
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