24281-07-0Relevant articles and documents
Lewis basic selenium catalyzed chloroamidation of olefins using nitriles as the nucleophiles
Tay, Daniel Weiliang,Tsoi, Ivan Tan,Er, Jun Cheng,Leung, Gulice Yiu Chung,Yeung, Ying-Yeung
supporting information, p. 1310 - 1313 (2013/04/24)
A Lewis base catalyzed chloroamidation of olefinic substrates was achieved using diphenyl selenide as the catalyst. The reaction conditions are mild and suitable for a wide range of substrates including those which are acid labile.
Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T
Abe, Takumi,Takeda, Hiroyuki,Miwa, Yoshihisa,Yamada, Koji,Yanada, Reiko,Ishikura, Minoru
experimental part, p. 233 - 241 (2010/05/14)
It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N1-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyc
New method for chloroamidation of olefins. Application in the synthesis of N-glycopeptides and anticancer agents
Rawal, Girish K.,Kumar, Amit,Tawar, Urmila,Vankar, Yashwant D.
, p. 5171 - 5174 (2008/09/17)
(Chemical Equation Presented) Chloroamidation of olefins using a new reagent system (COCl)2-AgNO3-CH3CN was observed. Various glycals with this reagent system produce 2-chloro-1-acetamido sugars in good yields which, in turn, were converted to free amino derivatives and various glycopeptides. The acetamido sugar derivatives and free amines were found to be promising anticancer agents against the U-87 malignant glyoma (a brain tumor) cell line with IC-50 = 1 nm-22 μM, and they were found to be far less cytotoxic against a normal human embryonic kidney cell line.
A general process for the haloamidation of olefins. Scope and mechanism
Yeung, Ying-Yeung,Gao, Xuri,Corey
, p. 9644 - 9645 (2007/10/03)
A methodology is described for the addition of a bromine atom and an amide nitrogen in a trans sense to an olefinic double bond. The process, which is illustrated by numerous examples, involves the use of an N-bromoamide and a Lewis acid as a source of Br
Addition reactions of nitryl chloride at multiple bonds
Zyk,Bondarenko,Nesterov,Zefirov
, p. 980 - 986 (2007/10/03)
Published data on additio of nitryl chloride to alkenes and possible reaction mechanisms were analyzed. Reactions of nitryl chloride with alkenes differing in the ionization potentials of the double bond and in the abilities to undergo various structural rearrangements were studied. Nitryl chloride was shown to be very sensitive both to the substrate and to the reaction conditions.
CIS 1,2-FUNCTIONALIZATION OF CYCLOHEXANE USING SELENIUM INTERMEDIATES
Morella, Angelo M.,Ward, A. David
, p. 2899 - 2900 (2007/10/02)
The trans 1,2-phenylseleno acetate, acetamide, alcohol and nitrile of cyclohexane may be oxidized at selenium by halogens and the phenylseleno moiety displaced by halide to give high yields of 1,2 halide-containing products with cis geometry.
The photochemical addition of N-haloamides to olefins: the influence of various factors on the competition between 1,2-addition and hydrogen abstraction
Lessard, Jean,Mondon, Martine,Touchard, Daniel
, p. 431 - 450 (2007/10/02)
In the photodecomposition of N-haloamides (ZCONRX) in the presence of olefins, the 1,2-addition chain competes with the hydrogen abstraction chain(s) leading to the parent amide (the quantum yields for these processes are greater than unity).The following factors were shown to have an influence on this competition as measured by the yield of 1,2-addition and the yield of parent amide in methylene chloride solutions: (i) the N-halogen (higher yields of addition with X=Cl than with X=Br); (ii) the electronegativity of Z (increase of the yield of addition as the electronegativity of Z increases); (iii) the temperature (higher yields of addition at lower temperatures, and at -70 degC, better yields of addition (>90percent, R=H) for X=Br than for X=Cl); and (iv) the size of R (dramatic decrease of the yield of 1,2-addition in going from R=H to R=CH3).Surprisingly, the presence of a scavenger for HX had no influence on the yield of 1,2-addition.Both the size and electronegativity of Z had an effect on the stereochemistry of 1,2-addition to cyclohexene.High yields of addition to a variety of olefins were obtained with N-chloroamides such as ClCH2CONHCl, C2H5OCONHCl, CF3CONHCl.Their addition to enol ethers at -70 degC led to the synthesis of α-amido acetals or ketals (aldehydes or ketones) and to an α-amido glycoside in good yields.
