Amines trapping reagents

However, King et al. (1977) have shown that in some cases one can get abnormal addition and the formation of substituted sulfinic acids (Scheme 4). Abnormal addition, for example, is involved as the first step in the complex pathway (207) by which sulfine [90] is formed from PhCH=S02 when phenylmethanesulfonyl chloride is treated with a tertiary amine in the absence of any of the normal sulfene-trapping reagents (King and Harding, 1976). 

In the reaction of alkynyl thiolates (39) with excess diethylamine, the amine provides the proton to generate an aldothioketene (40) and, at the same time, serves as the trapping reagent (Scheme 9). Bis(trimethylsilyl)thioketene (41) gives a smooth reaction with amines, but one silyl group is always displaced in the process yielding thioamides (42 equation 17). ... 

C.viii. Amines, Amides, Imides, and Sulfonamides as the H—Y Trapping Reagents Intermolecular Diene Dimerization... 

Generally, more basic amines are better trapping reagents than less basic ones, and consequently, the reaction of ammonia or a primary amine does not stop after the addition of one octadienyl moiety the resulting monooctadienylated amine product reacts faster than the starting amine. Thus, for ammonia, one typically forms the tertiary octadieny-lamine as the major product. For example, butadiene and ammonia (10 1) un-... 

Electrophilic Silylation Reagent. l,2-Bis(chlorodimethyl-silyl)ethane is not only an effective amine silylating reagent, but can also be employed in reactions with other anions. For example, when treated with the silver sulfonate salt as in eq 11, the nonafluorobutanesulfonic acid silyl ester (27), an extremely powerful silylating reagent, results.Carbanions are also effectively trapped by (1) A series of rigid butadiene Diels-Alder precursors such as (28) have been prepared in this fashion as outlined in eq 12.12... 

For example, Chang s group used simple amines [55], alcohols [56], and water [57] as trapping reagents to perform three-component reactions, obtaining amidates 86, imidates 87, and amides 88, respectively (Scheme 5.57). 

In solution, l-(ot-aminoalkyl)benzotriazoles 562 are in equilibrium with iminium cation 563 and hence with their benzotriazole-2-yl isomers 564 (Scheme 89). Protonation or complexation of the benzotriazolyl moiety (e.g., Mg, Zn, B, A1 reagents) facilitates the transformation. Intermediate iminium cations 563 can be trapped by nucleophiles providing synthetic pathways to various amines. Many such reactions are described in CHEC-II(1996) <1996CHEC-11(4)1 >, and some newer results are compiled in reviews <2005T2555>. 

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