86766-74-7

Upstream product

• 1521-51-3 rac-3-bromocyclohexene 
• 74-89-5 methylamine 
• 118149-88-5 N-Cyclohex-2-enyl-N-methyl-hydroxylamine 
• 86766-64-5 N-(cyclohex-2-enyl) methyl carbamate 
• 51479-76-6 cyclohex-2-en-1-yl 2,2,2-trichloroacetimidate 
• 59874-94-1 1-(2',2',2'-trichloromethylcarbonylamino)cyclohex-2-ene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 930-68-7 cyclohexenone 
• 822-67-3 Cyclohex-2-enol 
• 133165-64-7 2,2,2-trichloro-N-cyclohex-2-en-1-yl-N-methylacetamide 
• 1541-28-2 3-<(ethoxycarbonyl)amino>cyclohexene 

Downstream Products

• 147949-54-0 N-(Cyclohex-2-en-1-yl)-N-methyl-α-(phenylthio)acetamide 
• 129920-33-8 α,α-dichloro-N-(cyclohex-2-en-1-yl)-N-methylacetamide 
• 1196-52-7 7-Methyl-cis-7-azabicyclo<4.3.0>nonan-8-one 
• 133165-63-6 N-(2-cyclohexen-1-yl)-2-iodo-N-methylacetamide 
• 134339-75-6 (3R^*,3aR^*,7aS^*)-Octahydro-1-methyl-3-(phenylthio)indol-2-one 
• 127218-42-2 2-Chloro-N-cyclohex-2-enyl-N-methyl-2-phenylsulfanyl-acetamide 

Relevant academic research and scientific papers

Aryne-Mediated [2,3]-Sigmatropic Rearrangement of Tertiary Allylic Amines

A new strategy has been established for the [2,3]-sigmatropic rearrangement of quaternary allylic ammonium ylides via in situ activation of tertiary allylic amines with arynes under mild conditions. Using 2-(trimethylsilyl)aryl triflates as aryne precurso

Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

The deprotonation of N′-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N′-aryl substituent from N′ to the allylic position α to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcyclohexenamines.

Complex polycyclic lactams from pericyclic cascade reactions of Zincke aldehydes

(Chemical Equation Presented) In the course of a simple mechanistic study on the rearrangement of Zincke aldehydes to Z-α,β,γ,δ- unsaturated amides, a thermally induced pericyclic cascade rearrangement that converts Zincke aldehydes derived from allylic and homoallylic amines into polycyclic lactams was discovered. The key reaction involves an E-Z alkene isomerization, a 6? electrocyclic ring closure, a[1,5]-sigmatropic shift of hydrogen, a 6? electrocyclic ring-opening , and a Diels-Alder cycloaddition, and proceeds with excellent stereoselectivity. The unusual observation that furans and an indole serve as dienophiles in this cascade reaction permitted the synthesis of complex, functional group-rich tri- and tetracyclic lactams. In all cases, the rigid polycyclic products are available in only two steps from pyridinium salts and the allylic or homoallylic secondary amines.

Effect of Temperature on Atom Transfer Cyclization Reactions of Allylic α-Iodo Esters and Amides

Atom-transfer cyclizations of allyl iodoacetates and N-allyl-N-methyliodoacetamides are much more efficient at 80 deg C than at 25 deg C.At 80 deg C, β-(iodomethyl) lactones and lactams are formed rapidly and in good yield under standard atom-transfer conditions (sunlamp irradiation of iodide and 10percent hexabutylditin in benzene for 10-60 min).It is proposed that this temperature effect is responsible for some unusual observations by Jolly and Livinghouse in the cyclization of N-cyclohexenyl-N-methyliodoacetamide.The results suggest that the beneficial effect of temperature arises because an increase in the rate of rotation of t he OC-O or OC-N bond in the intermediate radicals begins to convert syn radicals (which cannot cyclize) to anti radicals (which can cyclize).Consistent with this hypothesis, the radical derived from N,N-diallyliodoacetamide (which always has a favorable arrangement for cyclization) closes with excellent efficiency at 25 deg C.

Radical Cyclization of N-(Cyclohex-2-enyl)-α,α-dichloroacetamides. Stereoselective Syntheses of (+/-)-Mesembranol and (+/-)-Elwesine

Stereoselective syntheses of the Sceletium alkaloid (+/-)-mesembranol (2) and the Amaryllidaceae alkaloid (+/-)-elwesine (3) have been achieved.A key step in the syntheses involves the Bu3SnH-mediated radical cyclization of the dichloroacetamides 34 and 4

PALLADIUM(0)-CATALYZED HYDROXYLAMINATION OF ALLYL ESTERS. SYNTHESIS OF N-ALLYLHYDROXYLAMINES AND SECONDARY ALLYLAMINES

Palladium-catalyzed reaction of allyl esters with hydroxylamines gives N-allylhydroxylamines, which are readily converted into secondary allylamines upon treatment with zinc powder in a dilute HCl solution.