Reactivity of α‐Bromosulfones Obtained from  gem ‐Dibromides | Zendy

Münster Niels | Zendy; Werel Laura | Zendy; Rennar Georg Alexander | Zendy; Harms Klaus | Zendy; Koert Ulrich | Zendy

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Reactivity of α‐Bromosulfones Obtained from gem ‐Dibromides

Author(s) -

Münster Niels,

Werel Laura,

Rennar Georg Alexander,

Harms Klaus,

Koert Ulrich

Publication year - 2015

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201501136

Subject(s) - chemistry , steric effects , stereoselectivity , reactivity (psychology) , bromine , medicinal chemistry , chelation , substitution reaction , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology

α‐Bromosulfones have been synthesized diastereoselectively by reaction of β‐hydroxy gem ‐dibromides with aromatic sulfinates. More steric demanding groups in the β‐position led to increased stereoselectivity in these S N 2 reactions. Lithiated α‐bromosulfones react diastereoselectively with alkylating agents, aldehydes, and ketones. No configurational stability of the lithiated α‐bromosulfones was observed except fast equilibration towards a chelate‐stabilized intermediate. Treatment of the α‐bromosulfone with methylcuprate resulted in substitution of the bromine by a methyl group.

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