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Fluorinated Isocyanates and Their Derivatives as Intermediates for Biologically Active Compounds

1977; Wiley; Volume: 16; Issue: 11 Linguagem: Inglês

10.1002/anie.197707353

1521-3773

E. Kühle, E. Klauke,

Sulfur-Based Synthesis Techniques

Abstract Fluorinated aromatic isocyanates are valuable intermediates for the production of herbicides and insecticides. Unexpected rearrangements during the synthesis of 2‐(trifluoromethyl)phenyl isocyanates provide an entry to N ‐trifluoromethylaminobenzoyl fluorides, a novel class of compounds having fungicidal properties. Carbamoyl fluorides, the products of HF addition to isocyanates, undergo ready sulfenylation. Use of these intermediates for the synthesis of N ‐sulfenylcarbamate insecticides led to the discovery of the new principle of detoxification of carbamates by sulfenylation.