Convenient Preparation of N-Monosubstituted S,S-Diarylsulfodiimides Using Fluoro-λ⁶-sulfanenitriles

Abstract

The reaction of fluorodiphenyl-l 6 -sulfanenitrile with primary alkyl-or aryl-amines in the presence of acid catalysts or tertiary amines gave N-monosubstituted S,S-diphenylsulfodiimides effectively.

S,S-Diphenyl-N-tosyl sulfone diimine

“…data reports diphenyl-S-pyrrolidinoiminosulfonium perchlorate [1.503 (2) Å for S-N (NH), X-ray; Sheikh et al., 2017] and S,S-diphenylsulfodiimide-N-phenyl [1.526 Å for S-N (NH) and 1.546 (1) Å for S-N (Ph), X-ray; Yoshimura et al, 2008], and shorter than that of S,S-diphenyl-N-tosylsulfilimine (1.628 Å , X-ray; Ká lmá n et al, 1971). The N1-S2-N2 bond angle [126.05 (9) ] is larger than 109.5 , while the N-S-C and C-S-C bond angles [102.92 (9)-112.96 (19) ] are close to 109.5 .…”

N-Ethyl-N′-(3-methylbenzoyl)-S,S-diphenylsulfodiimide

“…data reports (1.462 Å ;Yoshimura et al, 1997), and close to the S N double bonds of S,S-dimethylsulfonediimine (1.533 Å , electron diffraction; Oberhammer et al, 1970), S,S-diphenyl-Spyrrolidinoiminosulfonium perchlorate [1.503 (2) Å for S-N (NH), X-ray; Sheikh et al, 2017] and S,S-diphenylsulfodiimide-N-phenyl [1.526 Å for S-N (NH) and 1.546 (1) Å for S-N (Ph), X-ray; Yoshimura et al, 2008], and shorter than the S-N bond of S,S-diphenyl-N-tosylsulfilimine (1.628 Å , X-ray; Ká lmá n et al, 1971). The N-S-N bond angles are larger than 109.5 expected for the sp 3 hybrid configuration, while the N-S-C and C-S-C bond angles are smaller.…”