Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

• Malcolm J. D’Souza and
• Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132, doi:10.3762/bjoc.18.13

• . The solvolyses of these additional types of sulfur(VI) substrates will be the topics of a future review. Keywords: correlation; Grunwald–Winstein equation; Hammett equation; mechanism; solvolysis; sulfonyl halides; Review 1. Introduction to solvolyses of sulfonyl halides In medicinal chemistry

• (1961–1971), Hambly and co-workers, published a series of eight papers (Solvolysis of Sulfonyl Halides, Parts I through VIII) [16][17][18][19][20][21][22][23]. In the initial study [16][17] of the solvolysis of the parent benzenesulfonyl chloride and the p-methyl, p-bromo-, and p-nitro derivatives in

• was considered to indicate more bond breaking at the transition state for the departure of the chloride ion in the hydrolyses of the sulfonyl chlorides. The sulfonyl halides are not ideal substrates for studies of this type since they range from poorly soluble to almost insoluble in water. The parent

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• disulfide, thioamide derivatives and sulfides Disulfides and thiosulfates Sulfoxides Sulfinic acids, sulfinate salts and sulfinamides Sulfonyl halides, sulfonyl hydrazines, thionyl chloride and sulfur dioxide C–S bond formations initiated by irradiation with light of wavelengths shorter than 380 nm or by

• two arenes with different nucleophilicity, which were reacted with one sulfinamide. The respective product with the stronger nucleophile is formed exclusively. In reactions with two arenes having similar nucleophilicity a mixture of the respective products was obtained. Sulfonyl halides and