Premium
A Truly Multifunctional Heterocycle: Iminophosphorane, N,P Chelate, and Dihydropyridine
Author(s) -
Smith Dan A.,
Batsanov Andrei S.,
Miqueu Karinne,
Sotiropoulos JeanMarc,
Apperley David C.,
Howard Judith A. K.,
Dyer Philip W.
Publication year - 2008
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/anie.200803373
Subject(s) - acetylene , dihydropyridine , tautomer , cycloaddition , chemistry , ring (chemistry) , chelation , stereochemistry , cleavage (geology) , bond cleavage , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , calcium , fracture (geology) , composite material
Three in one : The anellated σ 4 ‐1λ 5 ‐[1,3,2]diazaphosphole 2 exists in tautomeric equilibrium with isomer 1 (see scheme) and undergoes three completely different types of reaction: trimethyl aluminum binds at the N terminus of the PN bond with ring retention, the dihydropyridine fragment reacts with an activated acetylene in a pseudo‐[2+2] cycloaddition, and PN bond cleavage is possible with Rh I .