Issue 0, 1971

Crystal structure of a cyclopentenylidenephosphorane isolated from the reaction of tri-p-tolylphosphine and dimethyl acetylenedicarboxylate

Abstract

The product from the reaction of tri-p-tolylphosphine and excess of dimethyl acetylenedicarboxylate has been shown by X-ray crystallography to be trimethyl 3-methoxy-4-oxo-5-(tri-p-tolylphosphoranylidene)cyclopentene-1,2,3-tricarboxylate. The crystals were monoclinic with a= 17·60(1), b= 11·439(6), c= 31·67(2)Å, β= 107·11(2)°, and Z= 8 in space group C2/c. The refinement was terminated at an R factor of 14·8% by use of isotropic temperature parameters and with toluene residues treated as rigid groups. The P[double bond, length as m-dash]C bond of length 1·728(8)Å is part of a conjugated system involving C[double bond, length as m-dash]C in the cyclopentenyl ring, the 2-methoxycarbonyl substituent, and the carbonyl group at C(4). Some bond angles are larger than normal owing to mutual repulsion of adjacent substituents of the cyclopentenyl ring.

Article information

Article type
Paper

J. Chem. Soc. C, 1971, 2461-2464

Crystal structure of a cyclopentenylidenephosphorane isolated from the reaction of tri-p-tolylphosphine and dimethyl acetylenedicarboxylate

O. Kennard, W. D. S. Motherwell and J. C. Coppola, J. Chem. Soc. C, 1971, 2461 DOI: 10.1039/J39710002461

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