69257-64-3Relevant academic research and scientific papers
Enantioselective protonation of samarium enolates derived from α- heterosubstituted ketones and lactone by SmI2-mediated reduction
Nakamura, Yutaka,Takeuchi, Seiji,Ohgo, Yoshiaki,Yamaoka, Makoto,Yoshida, Akihiro,Mikami, Koichi
, p. 4595 - 4620 (2007/10/03)
SmI2-mediated reductive cleavage of α-heterosubstituents of α-alkyl or α-aryl ketones and lactone gave the corresponding 'thermodynamic samarium enolates'. Enantioselective protonation of the samarium enolates with C2- symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.
SUBSTITUENT EFFECTS ON THE REGIO- AND STEREOSELECTIVITY OF GAS-PHASE ACID-INDUCED RING OPENING IN 1-ARYLCYCLOHEXENE OXIDES
Cecchi, P.,Pizzabiocca, A.,Renzi,G.,Chini, M.,Crotti, P.,et al.
, p. 4227 - 4234 (2007/10/02)
Comparative analysisof the ratio of the isomeric monomethyl ethers of 1-arylcyclohexane-1,2-diols formed in the gas-phase and solvolytic acid-induced methanolysis of several 1-arylcyclohexene oxides indicates the intrinsic electronic factors detrminimg the regio- and stereochemical course of the nucleophilic attack, related to the partial degree of carbocationic character at the reaction centre in the substitution transition state.
Photochemical Reactions of Contact Charge-Transfer Pairs of 1-Arylcyclohexenes and Oxygen
Kojima, Masanobu,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 3331 - 3336 (2007/10/02)
Photoexcitation of contact charge-transfer (CCT) pairs of 1-arylcyclohexenes 1 (aryl: phenyl, 4-methylphenyl, and 4-methoxyphenyl) and oxygen in acetonitrile and benzene gave 1,2-epoxy-1-arylcyclohexanes 2 as major products together with 2-aryl-2-cyclohexen-1-ols and acetophenones 4.Similar irradiation of the CCT pairs in methanol/acetonitrile afforded mainly 2-aryl 2-cyclohexen-1-ones, and 4.The formation of these products can be explained by photoinduced electron transfer in the excited CCT pairs generating radical cations of 1 and superoxide anions.
ANOMALOUS STEREOCHEMISTRY OF GASE-PHASE ACID-INDUCED RING OPENING IN 1-PHENYLCYCLOHEXENE OXIDE
Crotti, P.,Macchia, F.,Pizzabiocca, A.,Renzi, G.,Speranza, M.
, p. 3393 - 3396 (2007/10/02)
The first experimental evidence for an entropy-driven frontside displacement in a gas-phase cationic nucleophilic substitution has been provided by the results concerning the ring opening of 1-phenylcyclohexene oxide catalized by gaseous acids.
