44976-81-0Relevant articles and documents
Stereodynamics of Inversion and Rotation in Trialkylamines. N,N-Diisopropyl Primary Alkylamines Studied by Dynamic NMR Spectroscopy and Molecular Mechanics Calculations
Anderson, J. Edgar,Casarini, Daniele,Lunazzi, Lodovico
, p. 1791 - 1796 (1990)
From the temperature dependence of NMR spectra, two separate conformational processes can be distinguished and studied in N,N-diisopropylneopentylamine.A high-barrier inversion/ rotation process involves eclipsing of t-butyl and isopropyl groups, while a rotation process with a lower barrier involves lesser eclipsing interactions.Molecular mechanics calculations help illustrate the ground state conformations involved.Barriers are smaller when the neopentyl group is replaced by less branched primary alkyl groups.
A tertiary amine as a hydride donor: Trichlorosilyl triflate-mediated conjugate reduction of unsaturated ketones
Kotani, Shunsuke,Osakama, Kazuki,Sugiura, Masaharu,Nakajima, Makoto
supporting information; experimental part, p. 3968 - 3971 (2011/09/16)
Bulky tertiary amines, especially dicyclohexylisobutylamine, smoothly reduced α,β-unsaturated ketones in the presence of trichlorosilyl triflate to give the corresponding saturated ketones in excellent yields. Isotope-labeling studies revealed that an α-hydrogen of the amine was transferred to the enones during reduction.
Synthesis and Properties of Sterically Hindered Tertiary Amines and Guanidines
Wieland, Gerhard,Simchen, Gerhard
, p. 2178 - 2193 (2007/10/02)
Sterically hindered tertiary amines 7,8,14,17 are synthesized by reaction of the iminium salts 3,4, and 16 with Grignard compounds 5,12 or alkyllithium compounds 11,13.Hindered guanidines 24 are prepared from chloroformamidinium 22 or (dichloromethane)iminium salts 26 and primary amines 23.The pKa values of the amines 7,8,17, and guanidines 24 are measured, and their alkylation with methyl fluorosulfonate (31) is studied.