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J Am Chem Soc. 2007 Apr 25;129(16):5167-74. Epub 2007 Mar 29.

The synthesis of dichlorodiazirine and the generation of dichlorocarbene: spectroscopy and structure of dichlorocarbene ylides.

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1
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu

Abstract

Reaction of 2,4-dinitrophenoxychlorodiazirine (13) with chloride ions affords dichlorodiazirine (4). Photolysis of 4 generates dichlorocarbene. In laser flash photolysis (LFP) experiments, CCl2 forms chromophoric ylides or oxides with pyridine, 2-picoline, thioanisole, and oxygen. Spectroscopic and computational studies of the ylides are reported. The UV spectrum of CCl2 in solution, however, is not observed. It appears possible that CCl2 is rapidly captured by oxygen to afford a chromophoric dichlorocarbene carbonyl oxide. We present a theoretical analysis of this process.

PMID:
17391033
DOI:
10.1021/ja068727w
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