902259-32-9Relevant academic research and scientific papers
Carbon-13 and Oxygen-18 Kinetic Isotope Effects on Methanolysis of p-Nitrostyrene Oxide
Jacober, Stephen P.,Hanzlik, Robert P.
, p. 1594 - 1597 (1986)
Kinetic isotope effects for the acid- and base-catalyzed methanolysis of - and -p-nitrostyrene oxide have been measured at 30.0 deg C.In acid 94.7percent of the reaction occurs at the benzylic carbon, while in base 83.5percent occurs at the primary carbon (C(8)).In base the isotope effects k16/k18 and k12/k13 were 1.035+/-0.013 and 1.082+/-0.012, while in acid they were 1.012+/-0.011 and 0.995+/-0.012, respectively.These data complement previously determined deuterium isotope effects for the reaction in base.They suggest a late transition state in base with considerable ring opening via an SN2 mechanism.However, in acid, the data suggest a somewhat earlier transition state with less ring opening and weaker bonding to the nucleophile than in base.
Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides
Chen, Guohong,Wang, Xin,Jin, Xiaoqian,Liu, Lingyan,Chang, Weixing,Li, Jing
experimental part, p. 1294 - 1301 (2010/11/05)
This paper presents a versatile reagent for epoxide cleavage. The allyltin tribromide could act as a novel and easily prepared allylation reagent and halide atom donor to convert epoxides to the corresponding homoallyl alcohols and halohydrins in high yields with excellent regioselectivities under mild reaction conditions, respectively. It could also act as a Lewis acid to catalyze the ring opening reactions of epoxides with alcohols.
