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Convenient Syntheses of 2‐Nitrophenylsulfen‐(NPS‐)imines by Oxidation of NPS‐Protected Amines and Amino Acid Derivatives
Author(s) -
Heyer Joachim,
Dapperheld Steffen,
Steckhan Eberhard
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210913
Subject(s) - chemistry , nucleophile , electrochemistry , intramolecular force , combinatorial chemistry , stoichiometry , salt (chemistry) , nucleophilic addition , organic chemistry , catalysis , electrode
2‐Nitrophenylsulfenimines 2 of large structural variety are easily available from 2‐nitrophenylsulfenamides 1 , by direct and indirect electrochemical oxidation or by using stoichiometric amounts of a triarylamine radical cation salt. In most cases the direct electrochemical method is to be preferred, because of the convenient reaction procedure and the simple workup of the products. Inter‐ and intramolecular addition of nucleophiles to the C N double bond is possible as shown by two examples.