Premium
Umpolung of P−H Bonds
Author(s) -
Gudat Dietrich,
Haghverdi Asadollah,
Nieger Martin
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000901)39:17<3084::aid-anie3084>3.0.co;2-r
Subject(s) - umpolung , reactivity (psychology) , chemistry , regioselectivity , benzaldehyde , medicinal chemistry , stereochemistry , organic chemistry , catalysis , nucleophile , medicine , alternative medicine , pathology
The π‐electron delocalization in the diazaphospholenes 1 leads not only to a weakening of the P−H bond, but also to an umpolung of its reactivity. Thus, compounds 1 react with acids with elimination of H 2 , and display an inverse regioselectivity during the addition to benzaldehyde. R 1 =H, Cl; R 2 = t Bu, 2,4,6‐Me 3 C 6 H 2 .