Premium
Some ring expansion and related reactions of the phosphindole system
Author(s) -
Hughes Alan N.,
Amornraksa Kitti,
Phisithkul Siriporn,
Reutrakul Vichai
Publication year - 1976
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.5570130501
Subject(s) - chemistry , ring (chemistry) , sodium hydride , cleavage (geology) , hydroxide , sodium hydroxide , mass spectrum , hydride , context (archaeology) , phosphorus , sodium , medicinal chemistry , chloride , ion , organic chemistry , inorganic chemistry , hydrogen , paleontology , geotechnical engineering , fracture (geology) , engineering , biology
3‐Butyl‐1,2‐diphenylphosphindole reacts smoothly with ethyl propiolate and water and with benzoyl chloride and water to give ring expanded products. The second of these products is further expanded to a seven‐membered system by treatment with sodium hydride. With diiodo‐methane followed by hydroxide ion, cleavage of the phosphorus‐containing ring occurs. The nmr and mass spectral data are analyzed in detail and the results are discussed in the context of related studies with simple phospholes and dibenzophospholes. Some of the results further illustrate that predictions regarding the types of reaction entered into by phosphorus heterocycles must be made with caution.