Reaction with amide bases

Notice that water can act either as an acid or as a base, d.epending on the circumstances. In its reaction with HC1, water is a base that accepts a proton to give the hydronium ion, In its reaction with amide ion, -NH2, however,... 

In contrast to the borylation of alkane C-H bonds, the coupling of aryl halides with amines was based on a literature precedent from another group published about a decade before our initial studies. Kosugi, Kameyama and Migita published the coupling of aryl halides with tin amides." Mechanistic studies we conducted on this process led us to the perhaps obvious realization that the reaction" could be conducted with amines and a silylamide base instead of tin amides (equation 4)." Surveys of bases with similar p a values led Janis Louie to conduct reactions with alkoxide bases. Similar studies were conducted at nearly the same time by Steve Buchwald and coworkers."... 

The advantage of these complexes is that each Pt complex is isolated in pure form, and the crystal structure is known. Based on 1H-and 195Pt-NMR spectroscopy, the antitumor active compounds were found to be disrupted as shown in Fig. 20, giving finally [Pt(NH3)2(H20)2]2+, which is the same hydrolysis product as ds-DDP and is responsible for the activity. Therefore, the subsequent reaction with DNA bases and the mechanism would be the same with those of cis-DDP. The antitumor inactive compounds are relatively stable and are disrupted only to dinuclear amidate-bridged compounds. No further decomposition to [Pt(NH3)2(H20)2]2+ occurs. 

Dinitrogen monoxide can act as a Lewis base in complexes (monodentate in [Ru(NH3)5(N20)] +). It can also act as a Lewis acid with strong Lewis bases, for example, in the reaction with amides to form azides. 

Reaction between Two Different Ketones. This is seldom attempted with hydroxide or alkoxide bases in protic solvents since similar considerations apply to those discussed for aldehydes. This reaction is commonly done with amide bases in aprotic solvents, but with somewhat more difficulty than with aldehydes. 

The intramolecular aldol condensation is well known, and aldol reactions are often used to close five- and six-membered rings. Because of the favorable entropy (p. 303), such ring closures generally take place with ease when using hydroxide or alkoxide bases in protic solvents. In aprotic solvents with amide bases,... 

Many of the SrnI reactions studied to date have employed liquid ammonia as solvent. This is an attractive solvent because it allows weak carbon acids such as acetone to be converted completely to their conjugate bases by reaction with amide... 

Ring-opening of epoxides by P-elimination, on reaction with strong bases, such as lithium amides, or combinations of trimethylsilyl triflate with diazabicycloundecane, ° is a useful synthetic method to prepare allylic alcohols, particularly as it can be carried out enantioselectively. ... 

AMINOBENZENESULFONIC ACID or p-AMINOBENZENESULFONIC ACID (121-57-3) CsH NOjS HjO Decomposes on contact with strong acids, forming sulfur trioxide. The aqueous solution is acidic reaction with strong bases. Incompatible with alkylene oxides, aliphatic amines, alkanolamines, amides, ammonia, epichlorohydrin, organic anhydrides, isocyanates, oxidizers, vinyl acetate. On small fires, use dry chemical powder (such as Purple-K-Powder), Halon , water spray, or CO2 extinguishers. 

CjHyNOjS HjO Decomposes on contact with strong acids, forming sulfur trioxide. The aqueous solution is acidic reaction with strong bases. Incompatible with alkylene oxides, aliphatic amines, aUcanolamines, amides, ammonia, epichlorohydrin, organic anhydrides, isocyanates. 

BOLETIC ACID (110-17-8) C4H4O4 Combustible solid. Dust or finely divided material forms explosive mixture with air (flash point 446°F/230°C 1364°F/740°C Fire Rating 1). Violent reaction with all bases (exothermic reaction), including amines, amides, and inorganic hydroxides ... 

---