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8210997 
Journal Article 
Sulfinyl Fluoride: A Reagent for Fluorination and Introduction of the -S(O)F Group 
Mahmood, T; Shreeve, JM 
1985 
Yes 
Inorganic Chemistry
ISSN: 0020-1669
EISSN: 1520-510X 
24 
9 
1395-1398 
English 
Sulfinyl fluoride reacts to replace active hydrogen with fluorine in P-H and C-H bonds. However, with >N-H bonds, >NS(0)F is formed, e.g., with piperidine, 2, 6-dimethylpiperidine, 2, 2, 6, 6-tetramethylpiperidine, morpholine, 3, 5-dimethylmorpholine, and thiomorpholine. Fluorination occurs with oxidatively unsaturated compounds, such as trialkylphosphines and trialkyl phosphites to form difluorophosphoranes. The yields are reduced by side reactions of the phosphorus(III) species with the sulfur and sulfur dioxide that form concomitantly with the fluorination reaction. Sulfinyl fluoride and carbonyl fluoride are compared as fluorinating agents. © 1985, American Chemical Society. All rights reserved.