4088-37-3Relevant articles and documents
Reaction of lithium diethylamide with an alkyl bromide and alkyl benzenesulfonate: Origins of alkylation, elimination, and sulfonation
Gupta, Lekha,Ramirez, Antonio,Collum, David B.
supporting information; experimental part, p. 8392 - 8399 (2011/03/20)
A combination of NMR, kinetic, and computational methods are used to examine reactions of lithium diethylamide in tetrahydrofuran (THF) with n-dodecyl bromide and n-octyl benzenesulfonate. The alkyl bromide undergoes competitive SN2 substitution and E2 elimination in proportions independent of all concentrations except for a minor medium effect. Rate studies show that both reactions occur via trisolvated-monomer-based transition structures. The alkyl benzenesulfonate undergoes competitive SN2 substitution (minor) and N-sulfonation (major) with N-sulfonation promoted at low THF concentrations. The SN2 substitution is shown to proceed via a disolvated monomer suggested computationally to involve a cyclic transition structure. The dominant N-sulfonation follows a disolvated-dimer-based transition structure suggested computationally to be a bicyclo[3.1.1] form. The differing THF and lithium diethylamide orders for the two reactions explain the observed concentration-dependent chemoselectivities.
Joint Synthesis of Tertiary Unsymmetrical and Symmetrical Aliphatic Amines
Kozlov,Tereshko,Basalaeva,Tarasevich
, p. 1095 - 1098 (2007/10/03)
Tertiary unsymmetrical and symmetrical aliphatic amines were prepared by reaction of higher (C8-C16) and lower (C2-C4) aliphatic alcohols with nitriles containing the same number of carbon atoms as the lower aliphatic alcohols. Reaction conditions ensuring nearly quantitative yields of tertiary amines were determined.
