138749-92-5Relevant academic research and scientific papers
Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 14: Regioselectivity of the opening reactions with MeOH of remote O-substituted 1,2-epoxycyclohexanes under gas-phase operating conditions
Crotti, Paolo,Di Bussolo, Valeria,Favero, Lucilla,Pineschi, Mauro,Marianucci, Francesco,Renzi, Gabriele,Amici, Giuseppina,Roselli, Graziella
, p. 7513 - 7524 (2007/10/03)
The regiochemical behavior of cyclohexene oxides bearing a remote O-functionality was determined in the gas-phase in opening reactions with MeOH, using a gaseous acid (D3/+, C(n)H5/+, Me2F+
Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. 4. Synthesis and Reactions of the cis- and trans-Oxides Derived from 3-cyclohexene
Chini, Marco,Crotti, Paolo,Flippin, Lee A.,Gardelli, Cristina,Macchia, Franco
, p. 1713 - 1718 (2007/10/02)
The synthesis and nucleophilic addition reactions of diastereoisomeric title epoxides cis-7 and trans-8 were studied.While the ring-opening reactions of trans epoxide 8 are rationalized by means of steric, stereoelectronic, and conformational arguments, the analogous reactions of cis epoxide 7 indicate the ability of this isomer to react through chelated intermediates when metal salt catalyst is used.In 7 chelation reaction conditions led to a significant increase of nucleophilic attack on the C-1 oxirane carbon; the lack of reversal of the regiochemistry of the ring opening on passing from nonchelating to chelating reaction conditions suggests that cis epoxide 7 reacts through its more stable conformation in both of the two different operating conditions.
