ACIDITY OF BENZOYLCARBAMATES IN DIMETHYL-SULFOXIDE - CONFIRMATION OF MIXED N/O ALKYLATION IN THE MITSUNOBU REACTION

Seventeen benzoyl-, 4-methoxybenzoyl- and 4-nitrobenzoyl-carbamates have been synthesized via their corresponding isocyanates and their acidities determined in dimethyl sulfoxide solution. Their pK(a) values span an interval of nearly 5 pK units (10.4-15.2). Selected derivatives have been investigat...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 2 no. 4; pp. 655 - 658
Main Authors KOPPEL, KOPPEL, J, LEITO, PIHL, WALLIN, A, GREHN, L, RAGNARSSON, U
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1993
Royal Society of Chemistry
Subjects
Chemical reactivity
Chemistry
Chemistry, Organic
Chemistry, Physical
Exact sciences and technology
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
REAGENTS
Substituent effect
Benzenic compound
Aliphatic compound
Organic carbamate
Alkylation
Mitsunobu reaction
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Summary:Seventeen benzoyl-, 4-methoxybenzoyl- and 4-nitrobenzoyl-carbamates have been synthesized via their corresponding isocyanates and their acidities determined in dimethyl sulfoxide solution. Their pK(a) values span an interval of nearly 5 pK units (10.4-15.2). Selected derivatives have been investigated as amine synthons in the Mitsunobu reaction. In all cases mixtures of N- and O-alkylated products are obtained.
ISSN:1472-779X
0300-9580
2050-8239
1364-5471
DOI:10.1039/p29930000655