The Influence of Ring Size on the Selectivity of Phosphorus Heterocycle Aminolysis in the Presence of Water or Alcohols - Case of 2-Oxo- or 2-Thioxo-3-sulfonyl-1,3,2-oxazaphosphorinanes

Seven phosphorus heterocycles 2 were synthesized in one step by condensing PIV dichlorides 3 with N‐sulfonyl‐3‐aminopropanols 4. In the presence of water, they react selectively with the less bulky amines. No change in selectivity of aminolysis was observed when using these six‐membered heterocycles...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2006, Vol.2006 (8), p.1959-1964
Main Authors: Dujols, Frédéric, Mulliez, Michel
Format: Review
Language:English
Subjects:
Amino alcohols
Chemoselectivity
Phosphorus heterocycles
Phosphorylation
Sulfonamides
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Summary:Seven phosphorus heterocycles 2 were synthesized in one step by condensing PIV dichlorides 3 with N‐sulfonyl‐3‐aminopropanols 4. In the presence of water, they react selectively with the less bulky amines. No change in selectivity of aminolysis was observed when using these six‐membered heterocycles 2 instead of their five‐membered analogs 1. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500743