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Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions.

ABSTRACT: The selective ring-opening reaction of fluoroalkylidene-oxetanes was directed by the presence of the fluorine atom, enabling a two-step access to tetrasubstituted fluoroalkenes with excellent geometry control. Despite its small van der Waals radii electronic, rather than steric influences of the fluorine atom governed the ring-opening reaction with bromide ions, even in the presence of bulky substituents.

SUBMITTER: Fontenelle CQ

PROVIDER: S-EPMC7418098 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions.

Fontenelle Clément Q CQ Thierry Thibault T Laporte Romain R Pfund Emmanuel E Lequeux Thierry T

Beilstein journal of organic chemistry 20200807

The selective ring-opening reaction of fluoroalkylidene-oxetanes was directed by the presence of the fluorine atom, enabling a two-step access to tetrasubstituted fluoroalkenes with excellent geometry control. Despite its small van der Waals radii electronic, rather than steric influences of the fluorine atom governed the ring-opening reaction with bromide ions, even in the presence of bulky substituents. ...[more]

PMID: 32802210

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