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• 75-89-8 2,2,2-trifluoroethanol 
• 75621-35-1 (1-methyl-d3-cyclopentyl)methyl brosylate 
• 75621-38-4 (1-methyl-d3-cyclopentyl)methyl tresylate 
• 88766-96-5 Dilithiomethylen-cyclohexan 
• 67091-33-2 Bis(chlormercurio)methylen-cyclohexan 
• 88766-95-4 C₇H₁₀Br₂Hg₂ 
• 88766-99-8 C₁₅H₂₈Hg₂ 
• 1192-37-6 methylenecyclohexane 
• 52831-99-9 α-chlorocyclohexylcarbonyl chloride 

Relevant academic research and scientific papers

Iridium-catalyzed H/D exchange at vinyl groups without olefin isomerization

(Chemical Equation Presented) Making the switch: The title reaction represents a rare example of olefinic C-H activation without olefin isomerization. The conditions are sufficiently mild so that functional groups such as ketones, esters, nitriles, amines, sulfides, and alcohols are tolerated. This selectivity is demonstrated by deuterium labeling of several complex molecules.

Direct and Regioselective Transformation of α-Chloro Carbonyl Compounds into Alkenes and Deuterioalkenes

The successive treatment ethyl chloroacetate or chloroacetyl chloride with Grignard reagents and lithium powder leads to symmetrical terminal olefins in a regioselective manner.The best results are obtained with acid chlorides.The influence of the temperature and the reaction time on overall yield of the process are studied; in general, yields are increased by working at low temperature (-60 deg C).Internally substituted olefins are obtained from α-chloro acid chlorides through a similar process.The treatment of α-chloro aldehydes, ketones and carboxylic acid derivatives (esters or acid chlorides) with lithium aluminium hydride or lithium aluminium hydride/aluminium chloride and lithium powder at low temperature (-60 deg C) leads in a regioselective manner to olefins with the same carbon skeleton as the starting carbonyl compound.Reactions with lithium aluminium deuteride lead to incorporation of deuterium at predetermined positions in the alkene.

Deuterium Isotope Effects for Migrating and Nonmigrating Groups in the Solvolysis of Neopentyl-Type Esters

α- and γ-deuterium rate effects on the solvolysis of (1-methylcyclohexyl)methyl, (1-methylcyclopentyl)methyl, and (1-methylcyclobutyl)methyl sulfonate esters have been measured and the solvolysis products examined by 2H NMR spectroscopy.The results indicate that the products of the solvolysis of all these sulfonate esters are predominantely ((*) 98percent) rearranged.In the solvolysis of (1-methylcyclohexyl)methyl triflate, rearranged products with methyl migration slightly dominate over those with ring expansion.Normal isotope effects, 1.057 in 80E and 1.073 in 97T, are observed for the methyl-d3 compound and an inverse effect, 0,963, is observed in 80E for the methylene-d4 compound.However, in the solvolysis of both (1-methylcyclopentyl)methyl and (1-methylcyclobutyl)methyl sulfonates, the major products are those of ring expansion.In these examples, inverse effects are observed for the methyl-d3-labeled species.The observed isotope effects can be separated into respective values of 0.927, 0.913 for the nonmigrating methyl-d3 group and 1.177, 1.224 for the migrating methyl-d3 group in the solvolysis of (1-methylcyclohexyl)methyl triflate and (1-methylcyclopentyl)methyl brosylate.This explains the relative intramolecular migratory aptitudes of CH3/CD3 of 1.20 - 1.30 and the low γ-d9 isotope effect in the solvolysis of neopentyl sulfonates previously reported and makes them consistent with a mechanism which involves neighboring carbon participation during ionization.