72215-51-1

Basic information

• Product Name: 2,2,6,6-Tetradeuterio-1-methyl-cyclohexanol
• Synonyms: 2,2,6,6-Tetradeuterio-1-methyl-cyclohexanol
• CAS NO: 72215-51-1
• Molecular Weight: 118.156
• Mol File: 72215-51-1.mol

Chemical Properties

• CAS DataBase Reference: 2,2,6,6-Tetradeuterio-1-methyl-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,6,6-Tetradeuterio-1-methyl-cyclohexanol(72215-51-1)
• EPA Substance Registry System: 2,2,6,6-Tetradeuterio-1-methyl-cyclohexanol(72215-51-1)

Safety Data

• Hazardous Substances Data: 72215-51-1(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 917-64-6 methyl magnesium iodide 
• 1006-03-7 cyclohexanone-2,2,6,6-d4 

Downstream Products

• 1352223-16-5 C₇H₉⁽²⁾H₄Cl 

Relevant articles and documents

Solvolytic studies in cycloalkyl systems

The angular dependence of the C-H/C-D bond for a stabilization of the developing carbonium ion in the transition state of the solvolysis reaction of cycloalkyl halides has been investigated. This has been achieved by studying the rate of solvolysis of eight cyclic β-deuterated 1-alkyl-1-chloro cycloalkanes. Reaction rates for the solvolysis of both β-C-H and of the corresponding β-C-D compounds have been determined and the difference in the rate ratio i.e. kH/kD was attributed to the differential hyperconjugative effects exerted by β-hydrogens in different ring systems. By varying the ring size from C5 to C12 the dihedral angle of C-H bond in relation to the vacant "p" orbital on the trigonal carbon, (carbonium ion transition state) changes leading to changes in hyperconjugative stabilization of the intermediate carbonium ion with a consequent change in the rate of solvolysis. β-Deuterium isotope effects thus obtained for different cyclic systems were related with the actual bond angles between β-C-H bonds and the developing carbonium ions. Using the Allinger's force field calculations the best geometry for both the carbonium ions and the starting halo hydrocarbons were calculated.

1-Methyl-1-cyclohexyl Cations. Equilibria in Search of Structures

Solutions of the 1-methyl-1-cyclohexyl cation 1, by four independent criteria, show unequivocal evidence for a populated equilibrium involving two different "structures" of this cation.One of these criteria makes use of a remarkably large new equilibrium isotope effect, a method that should have general structural use in other carbocation systems.Unfortunately, our previous assignment of a chair and twist-boat conformation for the structures dose not accord with the new data.From an analysis of the 13C and 1H NMR shifts and KH/KD isotope effects for 1 and a series of ring-methylated analogues, it can be deduced that both structures are chair conformers and that one structure must involve extensive α-C-H hyperconjugation, while the other structure involves predominantly C-C hyperconjugation.The very existence of this type of isomerism in observable carbocations is unprecedented and has important implications for the field in general.