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The insertion and extrusion of heterosulfur bridges. XII. Selectivity and side reactions in the bridging process
Author(s) -
Klemm L. H.,
Pou Sovitj,
Detlefsen W. D.,
Higgins Clay,
Lawrence Ross F.
Publication year - 1984
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.5570210510
Subject(s) - chemistry , thiophene , sulfur , dibenzothiophene , hydrogen sulfide , toluene , substituent , bridging (networking) , sulfide , organic chemistry , amine gas treating , catalysis , polymer chemistry , computer network , computer science
1‐Phenylnaphthalene undergoes sulfur bridging at 500° in the presence of hydrogen sulfide and a heterogeneous catalyst to produce benzo[ b ]naphtho[1,2‐ d ]thiophene (13%). 3‐Methylphenanthrene and 9‐formylphenanthrene diethyl acetal ( 7b ) give sulfur bridging to produce phenanthro[4,5‐ bcd ]thiophene, i.e . with loss of the ring substituent. Additionally, 7b hydrogenolyzes to 9‐methylphenanthrene. With decadeuteriobiphenyl as a substrate, the dibenzothiophene formed, as well as the biphenyl recovered, is largely devoid of deuterium label. Confirmation that benzene and toluene react under sulfur‐bridging conditions is presented.