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Reactions of simple phospholes with dimethyl acetylenediearboxylate
Author(s) -
Holah David G.,
Hughes Alan N.,
Kleemola Daniel
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150816
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , ring (chemistry) , smiles rearrangement , computational chemistry , nucleophile , stereochemistry , organic chemistry , cycloaddition , catalysis
Reactions of the three phospholes 1‐phenylphosphole, 3‐methyl‐1‐phenylphosphole and 3,4‐dimethyl‐1‐phenylphosphole with dimethyl acetylenedicarboxylate are reported. All three phospholes react extremely readily with the acetylenic ester to give ring‐expanded bicyclic ylidic systems, although 1‐phenylphosphole appears to react by a different pathway from the other two phospholes. These reactions show that simple phospholes in general, in contrast to heavily substituted phospholes, are quite good nucleophiles in organic reactions and the results of this study are consistent with a relatively easily perturbed aromatic structure for these phospholes.