39165-19-0

Upstream product

• 75-25-2 Bromoform 
• 771-98-2 1-Phenylcyclohexene 
• 827-52-1 1-phenyl-1-cyclohexane 

Downstream Products

• 57293-39-7 1-Phenyltricyclo<4.1.0.0.^2,7>heptane 
• 57293-43-3 1-phenyl-1,3-cycloheptadiene 
• 57293-42-2 2-phenylcyclohepta-1,3-diene 
• 79929-93-4 exo-7-hydroxymethyl-1-phenylnorcarane 
• 79929-93-4 endo-7-hydroxymethyl-1-phenylnorcarane 
• 79929-94-5 endo-7-acetoxymethyl-1-phenylnorcarane 
• 79929-94-5 exo-7-acetoxymethyl-1-phenylnorcarane 
• 79929-92-3 1-phenylnorcarane-endo-7-carboxylic acid 
• 79929-92-3 1-phenylbicyclo[4.1.0]heptane-7-exo-carboxylic acid 
• 139344-38-0 syn-7-Brom-exo-6-methoxy-endo-6-phenylbicyclo<3.1.1>heptan 
• 139233-16-2 endo,endo-7-bromo-6-methoxy-6-phenylbicyclo<3.1.1>heptane 
• 139233-19-5 2-methoxy-1-phenylbicyclo<4.1.0>heptane 
• 139233-13-9 endo-6-methoxy-6-phenylbicyclo<3.1.1>heptane 
• 136258-36-1 2-phenyl-3-(2,2-dichlorovinyl)-1-cyclohexene 

Relevant academic research and scientific papers

Stereoselective ultrasonically induced reductive monosilylation of geminal dibromonorcaranes. Steric effects

Sonochemical reductive silylation of 1-R-7,7-dibromonorcaranes (R=H, Me, Et, i-Pr) by magnesium produces in each case two 7-bromo-7-trialkylsilylnorcaranes (alkyl=methyl or ethyl). The major isomer is exo (the trialkylsilyl group is cis to the R substituent), but the stereoselectivity of silylation decreases as the alkyl group size at C-1 increases. 1-Phenyl-7,7-dibromonorcarane produced a mixture of phenylcycloheptadienes and monobromonorcaranes.

Reaction of Organoaluminium Reagents with Cyclopropylmethyl Acetates and 2-Vinylcyclopropane-1,1-dicarboxylate Esters

Ring-opening alkylation of cyclopropylmethyl acetates was studied.The acetoxyl group of 7-(1-acetoxyheptyl)norcarane is substituted by the alkyl group upon treatment with trialkylaluminium, but alkylation of trans-1-(1-acetoxyethyl)-2-phenylcyclopropane with trialkylaluminium gives rise to trans-5-phenyl-2-alkenes.The reaction of (1S,2S)-2-phenylcyclopropylmethyl acetate with trimethylaluminium resulted in the complete loss of optical activity to give racemic 4-phenyl-1-pentene.Alkylation of trans-1-(1-acetoxy-3-phenylpropyl)-2-vinylcyclopropane with trialkylaluminium proceeds under regioselective ring-opening to give 3-alkylated trans-8-phenyl-1,5-octadiene (selectivity 73-83percent).The regio- and stereochemistry of homoconjugate addition to activated vinylcyclopropanes having a doubly carbonyl substituted ring carbon was studied.Trialkylaluminium on addition to diethyl 2-vinylcyclopropane-1,1-dicarboxylate in a 1,5-manner afford diethyl (2-alkyl-3-butenyl)propanedioate (over 96percent selectivity).In contrast, the reaction of this cyclopropane with tetraalkylaluminiumlithium takes place in a 1.7-manner to give diethyl (trans-4-alkyl-2-butenyl)propanedioate with 88-92percent selectivity.Clean regiocontrol of the reaction is observed in the methylation of ethyl exo-6-(trans-1-propenyl)-2-oxobicyclo(3.1.0>hexane-1-carboxylate with trimethylaluminium or tetramethyl aluminiumlithium.Alkylation with trimethylaluminium proceeds with 86percent inversion of the configuration at C(6) of the substrate, affording (2R*,3R*)-2-ethoxycarbonyl-3-cyclopentanone which is transformed into neonepetalactone.