107415-63-4Relevant articles and documents
AMINOLYSIS OF VINYLAMMONIUM SALTS. EFFECTS OF STRUCTURE AND MEDIUM
Kravchenko, V. V.,Popov, A. F.,Kotenko, A. A.
, p. 1332 - 1336 (2007/10/02)
The kinetics of the aminolysis of a series of vinylammonium salts ZCH=CHN+R3*X- were investigated in polar solvents and in water at 25 deg C.A quantitative assessment was made of the effect of the nature of the medium and the structure of activating group Z on the rate of the investigated processes.The aminolysis rate of the salts increases with increase in the donating characteristics of the solvent on account of the greater stabilization of the transition state compared with the initial state.Increase in the accepting characteristics of the medium leads to retardation of the process as a result of increase in the electrophilic solvation of the amine in the initial state.
2-HALOVINYL ARYL SULFONES: NEW COUPLING REAGENTS FOR CARBOXAMIDE FORMATION
Shimagaki, Masayuki,Koshiji, Hiroko,Oishi, Takeshi
, p. 45 - 58 (2007/10/02)
E-2-Chlorovinyl p-nitrophenyl sulfone 6 and 2-bromo-2-trifluoromethylvinyl phenyl sulfone 7a reacted with carboxylic acids in the presence of a molar equiv of Et3N affording the corresponding 2-acyloxyvinyl sulfones 8, 11, 17, 18, 22, 25, 28 and 29.The latter, on treatment with amines, gave amides 9, 13, 19, 23 and 26 and peptides 30 and 32.These reagents 6 and 7a were also used for the formation of N-methylanilides 13d, 13e, 19d, 23 and 26.Particularly, 6 was successfully used for synthesis of a macrocyclic lactam 23 involving a N-methylanilide moiety.The amidation reac tions proceeded under essentially neutral conditions.Therefore, base-sensitive β-hydroxycarboxy-N-methylanilides such as 26, whose structural unit was involved in maytansine 5, could be prepared by the present method.The reagent 6 was also effective for the preparation of peptides such as Val-N-MeVal derivatives (e.g.32), which were difficult to prepare by other methods.
