Comprehensive Heterocyclic Chemistry IV 2022
DOI: 10.1016/b978-0-12-818655-8.00026-3
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Oxiranes and Oxirenes: Fused-Ring Derivatives

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Cited by 2 publications
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“…In the presence of an aqueous base, the nucleophile (H 2 O) attacks the least substituted carbon atom based on an SN 2 -like reaction leading to ring-opening of the epoxide, whereas in the aqueous acid solution, the more substituted carbon is the site of nucleophilic attack according to the SN 1 displacement mechanism [59]. Similarly, epoxides undergo cleavage of the ether bond in the presence of anhydrous acids including HCl, HI, HBr to form halohydrin in the SN 1 -or SN 2 -like reactions, depending on whether the carbon attacked by the halogen anion is a primary, secondary or tertiary carbon [60,61].…”
Section: Important Reactions Of Epoxidesmentioning
confidence: 99%
“…In the presence of an aqueous base, the nucleophile (H 2 O) attacks the least substituted carbon atom based on an SN 2 -like reaction leading to ring-opening of the epoxide, whereas in the aqueous acid solution, the more substituted carbon is the site of nucleophilic attack according to the SN 1 displacement mechanism [59]. Similarly, epoxides undergo cleavage of the ether bond in the presence of anhydrous acids including HCl, HI, HBr to form halohydrin in the SN 1 -or SN 2 -like reactions, depending on whether the carbon attacked by the halogen anion is a primary, secondary or tertiary carbon [60,61].…”
Section: Important Reactions Of Epoxidesmentioning
confidence: 99%