C-3-symmetric azaphosphatranes

Citation
F. Lake et al., C-3-symmetric azaphosphatranes, COLL CZECH, 65(4), 2000, pp. 570-576
Citations number
25
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
00100765 → ACNP
Volume
65
Issue
4
Year of publication
2000
Pages
570 - 576
Database
ISI
SICI code
0010-0765(200004)65:4<570:CA>2.0.ZU;2-#
Abstract
C-3-Symmetric azaphosphatranes, (3S, 7S,10S)-2,3,7,8,9,10-hexamethyl-2,8,9- triaza-5-azonial-lambda(5)-phosphabicyclo[3.3.3]undecane chloride and (3S,7 S,10S)-3,7,10-triisopropyl-2,8,9-trimethyl -2,8,9-triaza-5-azonia-1-lambda( 5)-phosphabicyclo[3.3.3]undecane chloride, have been prepared starting from the corresponding chiral tripodal tetraamines and chlorobis-(diethylamino) phosphane. The compounds are weak acids which are not fully deprotonated by potassium tert-butoxide. Density functional calculations of the compounds and their conjugate bases demonstrate that the weak acidity originates in a conformational change upon deprotonation leading to substantial steric rep ulsion.