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Studies on the synthesis of heterocyclic compounds. VII. Action of acyl halides on heterocyclic compounds containing the O‐M‐O (M P, As, Sb) bond in the ring
Author(s) -
Anchisi Carlo,
Corda Luciana,
Maccioni Antonio,
Podda Gianni
Publication year - 1982
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.5570190127
Subject(s) - chemistry , reagent , halide , toluene , benzene , cleavage (geology) , antimony , ring (chemistry) , medicinal chemistry , solvent , bond cleavage , substrate (aquarium) , organic chemistry , stereochemistry , catalysis , geotechnical engineering , fracture (geology) , engineering , oceanography , geology
Abstract The action of acyl halides on heterocyclic compounds of five‐membered rings containing an O‐M‐O (M P, As, Sb) linkage is described. The reactions were either carried out in the presence of a solvent (benzene or toluene) or by direct heating of the reagent with the substrate. In the case of arsole, stibole and stannole derivatives, the cleavage of O‐M bond and the formation of the respective mono‐ and diesters were always obtained, while with the phospholes, no cleavage of the compounds was observed. The products IIa‐c (M = Sb) have been obtained in excellent yields starting from VIa‐c and antimony trichloride. The structure of the compounds which were prepared was determined by analytical and spectroscopic methods and also by comparations with authentic samples where possible.