101544-55-2

Basic information

• Product Name: 1-vinyl-cis-2-allylcyclohexanol
• CAS NO: 101544-55-2
• Molecular Weight: 166.263
• Mol File: 101544-55-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-vinyl-cis-2-allylcyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-vinyl-cis-2-allylcyclohexanol(101544-55-2)
• EPA Substance Registry System: 1-vinyl-cis-2-allylcyclohexanol(101544-55-2)

Safety Data

• Hazardous Substances Data: 101544-55-2(Hazardous Substances Data)

Upstream product

• 94-66-6 2-allylcyclohexan-1-one 
• 1826-67-1 vinyl magnesium bromide 
• 71404-48-3 (R)-2-((R)-1-Trimethylsilanyl-allyl)-cyclohexanone 
• 88298-13-9 (1R,2R)-2-((R)-1-Trimethylsilanyl-allyl)-1-vinyl-cyclohexanol 

Downstream Products

• 130741-49-0 ((1S,2R)-2-Allyl-1-vinyl-cyclohexyloxy)-trimethyl-silane 

Relevant articles and documents

A Copper(I)-Catalyzed Photobicyclization Route to exo-1,2-Polymethylene- and 7-Hydroxynorbornanes. Nonclassical 2-Bicycloheptyl and 7-Norbornyl Carbenium Ion Intermediates

A synthesis of 7-hydroxynorbornanes from 3-hydroxy-1,6-heptadienes is achieved by copper(I) trifluoromethanesulfonate catalyzed 2? + 2? photobicyclization and solvolytic rearrangement of intermediate cyclobutylcarbinyl alcohols.The rearrangements are remarkably stereoselective and stereospecific. exo-1,2-Polymethylene-7-hydroxynorbornanes are obtained stereoselectively from both cis- and trans-2-allyl-1-vinylcycloalkanols owing to rapid cis-trans epimerization at the 3-position of intermediate 2,3-polymethylenebicyclohept-2-yl carbenium ions.The importance of bridged (nonclassical) carbenium ion intermediates in the 2-bicycloheptyl to 7-norbornyl rearrangements is poignantly evidenced by stereospecific inversion at the migration origin which delivers 1,2,2-trimethylnorbornan-syn-7-ol in the face of a severe countervailing steric impediment.