The Journal of Organic Chemistry

Utilizing acetyl hypofluorite for chlorination, bromination, and etherification of the pyridine system

D Hebel, S Rozen

Index: Hebel, David; Rozen, Shlomo Journal of Organic Chemistry, 1991 , vol. 56, # 22 p. 6298 - 6301

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Citation Number: 56

Abstract

Acetyl hypofluorite, which is easily made from F2, possesses a strong electrophilic fluorine. This electrophile is able to attach itself to the nitrogen atom of pyridine and activate the ring toward nucleophilic attacks. The ultimate elimination of HF results in an overall easy nucleophilic displacement of the hydrogen of the important 2-position. The nucleophiles used; Clb, Brb, and Rob, originate from solvents such as CH2C12, CH2Br2, and various ...

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