7707-56-4

Upstream product

• 110-83-8 cyclohexene 
• 79-15-2 N-bromoacetamide 
• 75-05-8 acetonitrile 
• 21113-05-3 1-chloromercuri-2-acetamidocyclohexane 
• 77037-14-0 trans 2-acetamido-1-phenylselenocyclohexane 
• 108-24-7 acetic anhydride 

Downstream Products

• 74080-30-1 2-Amino-1-acetoxy-cyclohexan 
• 23547-20-8 cis-2-acetoxycyclohexylamine hydrobromide 

Relevant academic research and scientific papers

Lewis basic selenium catalyzed chloroamidation of olefins using nitriles as the nucleophiles

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.

Stereoselective one-pot synthesis of oxazolines

(Chemical Equation Presented) Treatment of alkenes with NBS, a nitrile, NaHCO3 and water in the presence of Cu(OTf)2 or Zn(OTf)2 is reported to furnish oxazolines in one pot and good yields. The reaction is equally applica

A general process for the haloamidation of olefins. Scope and mechanism

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

A comparative study on the reactivity of electrogenerated bromine with cyclohexene in acetonitrile and the room temperature ionic liquid, 1-Butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide

The reactivity of electrogenerated bromine with cyclohexene has been studied on a platinum microelectrode by linear sweep and cyclic voltammetry in both the room temperature ionic liquid, 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide, an

Bromination of Alkenes in Acetonitrile. A Rate and Product Study

The reaction of simple alkenes and aryl alkenes with molecular bromine in damp MeCN occurred with solvent incorporation to give 2-bromo-1-(N-acetylamino)alkanes, 2-methyloxazolines, 2-acetoxyalkylamine hydrobromides, and 2-(N-acetylamino) alcohols.These products arose by the transformation of initially formed 2-bromo-1-(N-acetylamino)alkanes obtained by MeCN attack on bromonium or bromocarbonium ions to give nitrilium tribromide salts.These reacted with water to give 2-bromo-1-(N-acetylamino)alkanes.The kinetic profile of the reaction showed a very fast initial reaction of the alkene and Br2 to yield the nitrilium tribromide, followed by a much slower reaction of Br3(1-) with the alkene.The incorporation of MeCN was Markovnikov and stereospecifically anti.The degree to which incorporation of solvent occurred depended upon the alkene structure and the initial reagent concentrations.A rationalization for the observed chemoselectivity and its dependence on the reaction conditions is offered.

BORON TRIFLUORIDE PROMOTED REACTIONS OF N-HALOELECTROPHILES WITH ALKENES

N-Haloelectrophiles react with alkenes in the presence of boron trifluoride etherate to give halofluorides and N-halo adducts.

CIS 1,2-FUNCTIONALIZATION OF CYCLOHEXANE USING SELENIUM INTERMEDIATES

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

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.