AlCl3-Mediated Aromatic Phenylthiation with N-Phenylthiophthalimide

Satoshi SUWA; Takeshi SAKAMOTO; Yasuo KIKUGAWA

doi:10.1248/cpb.47.980

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

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Volume 47 (1999) Issue 7
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Article overview

AlCl₃-Mediated Aromatic Phenylthiation with N-Phenylthiophthalimide

Satoshi SUWA, Takeshi SAKAMOTO, Yasuo KIKUGAWA

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Keywords: phenylthiation, N-phenylthiophtalimide, phenylsulfenium ion, modified neglect of diatomic overlap calcultion

JOURNAL FREE ACCESS

1999 Volume 47 Issue 7 Pages 980-982

DOI https://doi.org/10.1248/cpb.47.980

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Abstract

N-Phenylthiophthalimide reacts with AlCl₃ or TiCl₄ in areanes to give phenylthiated arenes alone via a phenylsulfenium ion intermediate, modified neglect of diatomic overlap (MNDO) molecular orbital calculations of which revealed that the positive charge preferentially populates the sulfur atom rather than the phenyl group in the phenylsulfenium ion.

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