C ‐Phosphorylated  N ‐(Trichloroethylidene)sulfonamides: A New Type of Highly Electrophilic Imines | Zendy

Rassukana Yuliya V. | Zendy; Onys’ko Petro P. | Zendy; Davydova Kateryna O. | Zendy; Sinitsa Anatolii D. | Zendy

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C ‐Phosphorylated N ‐(Trichloroethylidene)sulfonamides: A New Type of Highly Electrophilic Imines

Author(s) -

Rassukana Yuliya V.,

Onys’ko Petro P.,

Davydova Kateryna O.,

Sinitsa Anatolii D.

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400086

Subject(s) - chemistry , electrophile , intramolecular force , adduct , nucleophile , medicinal chemistry , phosphorylation , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry

A convenient preparative approach to previously unknown, highly electrophilic C ‐phosphorylated N ‐arylsulfonylimines 1 , based on fairly readily accessible α‐phosphorylated sulfonamides 5 , has been developed. Compounds 1 react with trialkyl phosphites or ethyl diphenylphosphinite in the aza‐Perkow reaction scheme to give C , N ‐diphosphorylated N ‐dichlorovinylsulfonamides 8 . On treatment with O‐ and S‐nucleophilic agents (alcohols, thiols, thiophenols), 1 forms addition products 12 and 15 , the functionalized derivatives of α‐aminophosphonic acids, while interaction between 1 and mercaptoacetic acid proceeds with intramolecular cyclization of the intermediate adduct to produce the novel 2‐phosphorylated thiazolidinones 17 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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