Unusual chemo- and stereo-selectivities in the reactions of 1,2-dichlorocyclopropenes with nitrile oxides
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 21,p. 2507-2508
- https://doi.org/10.1039/p19930002507
Abstract
1,2-Dichloro-3,3-dimethylcyclopropene reacts with a number of nitrile oxides to produce oxazines in moderate to good yield in a reaction which apparently involves an unusual formal 3-centre plus 3-centre cycloaddition of the dipole to an intermediate vinylcarbene. In contrast, 1,2-dichloro-3-chloromethyl-3-methylcyclopropene undergoes a dipolar cycloaddition to produce a 2-oxa-3-azabicyclo[3.1.0]-hex-3-ene in which the 6-chloromethyl substituent occupies the endo-position.Keywords
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