57293-42-2

Upstream product

• 6434-79-3 endo-7-Chlor-7-phenyl-bicyclo<4.1.0>heptan 
• 50786-01-1 cyclohepta-1,3-dien-2-yl trifluoromethanesulfonate 
• 100-58-3 phenylmagnesium bromide 
• 72657-59-1 6-Phenylbicyclo<3.2.0>heptan-6-ol 
• 104-15-4 toluene-4-sulfonic acid 
• 25308-75-2 1-Phenylcycloheptene 
• 1121-66-0 2-Cyclohepten-1-one 
• 771-98-2 1-Phenylcyclohexene 
• 39165-19-0 7,7-dibromo-1-phenyl-cis-norcarane 
• 536-74-3 phenylacetylene 
• 142-29-0 cyclopentene 

Relevant academic research and scientific papers

Addition of hypobromous acid to 1-phenylcycloalkenes

Reaction of 1-phenylcyclooctene and 1-phenylcycloheptene with N-bromosuccinimide (NBS) in aqueous DMSO gives the corresponding 3-bromo-2-phenylcycloalkenes and 2-phenylcycloalk-2-enols in a ratio of 3: 1. Unlike them, 1-phenylcyclohexene gives a mixture of 3-bromo-2-phenylcyclohexene and 2-bromo-1-phenylcyclohexanol. The oxidation of allylic alcohols with pyridinium chlorochromate afforded the corresponding α,β-unsaturated ketones.

An oxidative rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol to 1,1′-biphenyl-carbaldehydes: A mechanistic study

Acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol gave 1,1′-biphenyl and 1,1′-biphenyl-carbaldehydes in small amounts as well as the expected rearrangement products. A detailed study of the reaction mechanism revealed that the conversion occurs via an oxidative process through the consecutive formation of cycloheptadienes, cycloheptatrienes, and 1,1′-biphenyls. The acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0] hept-2-en-6-ols gave 1- and 2-phenylcycloheptatrienes directly, from which 1,1′-biphenyl and 1,1′-biphenyl-carbaldehydes were obtained by oxidation.

Cycloheptadiene Ring Synthesis by Tandem Intermolecular Enyne Metathesis

(Equation presented) The tandem intermolecular enyne metathesis between 1-alkynes and cyclopentene is reported, providing 2-substituted 1,3-cycloheptadienes. The success of the intermolecular reaction hinges on an appropriate balance between cycloalkene r

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.

A Versatile Route to 2-Substituted Cyclic 1,3-Dienes via a Copper(I)-Catalyzed Cross-Coupling Reaction of Dienyl Triflates with Grignard Reagents

A general synthesis of 2-substituted cyclic 1,3-dienes in two steps from α,β-unsaturated ketones has been developed. Formation of a dien-2-yl triflate followed by a copper(I)-catalyzed cross-coupling reaction with a Grignard reagent gives 2-substituted dienes in fair to excellent yields. Alkyl, aryl, and allyl Grignard reagents can be used.