39819-72-2

Upstream product

• 106348-43-0 (1S)-(-)-N-(cyclohex-2-en-1-yl)hydroxylamine 
• 75-05-8 acetonitrile 
• 110-83-8 cyclohexene 
• 4671-90-3 1-selenochroman-4-one 
• 76570-77-9 1-(phenylseleno)-2-acetamidocyclohexane 
• 124706-18-9 2-Bromo-N-cyclohex-2-enyl-N-(2,2,2-trifluoro-acetyl)-acetamide 
• 108-85-0 1-bromocyclohexane 
• 542-18-7 cyclohexyl chloride 
• 16717-84-3 3-azido-1-cyclohexene 
• 507-09-5 tiolacetic acid 
• 536-80-1 iodosylbenzene 
• 919-19-7 diethyl acetylphosphonate 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 132408-69-6 1-(2-cyclohexen-1-yl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester 

Downstream Products

• 1124-53-4 N-cyclohexylacetamide 

Relevant academic research and scientific papers

Synthesis of N-Protected Amino Esters via Palladium Catalysed Allylic Substitution

N-protected allylamines were prepared by palladium catalysed allylic substitution of the corresponding allyl acetates with a range of nitrogen nucleophiles.The so-formed N-protected allylamines were subjected to oxidative cleavage of the alkene to afford N-protected amino acids or esters.

Selenoxide Fragmentation Leading to Allylic Amides

Oxidation-fragmentation of β-amidoalkyl phenyl selenides produces allylic amides selectively.

Silver Salt-Mediated Allylation Reactions Using Allyl Bromides

A facile, efficient, and chemoselective synthesis of allylic amides has been developed. Allyl bromides were used as the precursors activated by silver triflate. A Ritter-type reaction readily proceeded to give various allyl amides under mild conditions. The reaction protocol was also applicable to different nucleophilic partners to give a wide range of allyl-substituted products in the absence of a base.

Iron-catalyzed olefin hydrogenation at 1 bar H2 with a FeCl3-LiAlH4 catalyst

The scope and mechanism of a practical protocol for the iron-catalyzed hydrogenation of alkenes and alkynes at 1 bar H2 pressure were studied. The catalyst is formed from cheap chemicals (5 mol% FeCl3-LiAlH4, THF). A homogeneous mechanism operates at early stages of the reaction while active nanoparticles form upon ageing of the catalyst solution. This journal is

Switching and Conformational Fixation of Amides Through Proximate Positive Charges

Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization. Taking charge of conformation: Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization.

The aza-wharton reaction: Syntheses of cyclic allylic amines and vicinal hydroxyamines from the respective acylaziridines

The Wharton reaction, initially described for acyl epoxides, has been studied using the structurally similar aziridines. By this reaction, a range of cyclic allylic amines and vicinal amino alcohols have been prepared stereoselectively and, in some cases, enantiomerically pure.

Novel, Regioselective Allylamine Construction; First Synthesis of Geranyllinaloisocyanide, a Diterpene from the Marine Sponge, Halichondria Sp.

The first synthesis of the diterpene, 3-isocyano-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene (geranyllinaloisocyanide, 1), has been achieved through an allyl cyanate-to-isocyanate rearrangement.The crucial step in this synthesis is in situ transformation of allyl isocyanates into stable allyl acetamides with trimethylaluminium.

Lewis acidic catalysts for olefin epoxidation by iodosylbenzene

A ferric complex, (Et3HN) FeIII(bpb)Cl2, has been synthesized, and its structure has been determined by X-ray crystallography. This complex and its inflate derivative, (Et3HN)FeIII(bpb)(OTf)2, are found to catalyze the epoxidation of a variety of olefins by iodosylbenzene, OIPh. These reactions give little allylic oxidation of cyclohexene and stereochemical retention with cis-stilbene. Al(OTf)3, a nonredox metal salt, has also been found to catalyze the epoxidation of cyclohexene by iodosylbenzene, and the reactivity is quite similar to that of Fe(OTf)3, which, we studied previously. In addition to epoxides, other products were observed. For the reactions containing Fe(OTf)3, Al(OTf)3, or (Et3HN) FeIII(bpb)(OTf)2, cis-1,2-cyclohexanediol ditrifilate and 3-acetamidocyclohexene were found. The amide oxygen in 3-acetamidocyclohexene was derived from iodosylbenzene as verified by isotopic labeling using 18OIPh. For the reactions containing (Et3HN) FeIII(bpb)Cl2 FeCl3, or AlCl3, trans-1,2-dichlorocyclohexane and 3-chlorocyclohexene were observed. 1,4-Diiodobenzene was found in all of the reactions. The presence of these products suggests strongly that the mechanisms of these reactions are related to those occurring between soluble iodine(III)-containing compounds and olefins in the absence of any metal catalysts. A new mechanisms that accounts for all of the products is proposed which involves electrophilic attack on the olefin by the iodine(III) center in a metal-iodosylbenzene complex. The reactions of PhI(OAc)2 with norbornenecarboxylic acid or nortornene in different solvents were also investigated. The products isolated were shown to be 5-(acetyloxy)-3,3a,4,5,6,6a-hexahydro-[3β,3aα,5α,6β, 6aα]-3,6-methano-2H-cyclopenta [b] furan-2-one (1), 5-acetamido-3,3a,4,5,6,6a-hexahydro-[3β,3aα,5α,6β, 6aα]-3,6-methano-2H-cyclopenta [b] furan-2-one (2), and exo-2-acetoxy-syn-7-acetamidonorbornane (3). The structures of 1 and 3 were determined by X-ray crystallography. The formation of these products provides additional evidence for the electrophilic character of iodine(III) compounds.

Asymmetric synthesis of primary amines from alkenes and chiral chloronitroso sugar derivatives

A variety of alkenes 5 - 15, 38, 39 react with chloronitroso sugar derivatives 1 - 3 regioselectively at ambient temperature to give chiral hydroxylamines in 60-80% yield. In addition to these products of a formal ene reaction joined by a subsequent hydro