Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
39.3.4.1.4.2 Variation 2: Via In Situ Formation of Alkanesulfinyl Chlorides from Dialkyl Disulfides

DOI: 10.1055/sos-SD-039-00272

Braverman, S.; Cherkinsky, M.; Levinger, S.Science of Synthesis, (200839218.

The alkanesulfinate esters 72 may be prepared directly by low-temperature chlorination of dialkyl disulfides in alcohols.[‌145‌,‌146‌] The synthesis involves converting the disulfide into the sulfinyl chloride, which, without isolation, reacts with the appropriate alcohol (Scheme 44). When the disulfide and chlorine are used in stoichiometric amounts with a small excess of alcohol, the crude esters are produced in 6085% yields. The crude esters thus prepared can be purified from sulfonyl chloride contaminants by treatment with an aromatic amine, such as p-toluidine. The low molecular weight alkyl alkanesulfinates are then best separated from the excess amine by distillation. Those of higher molecular weight and low water solubility can be extracted with dilute acid to remove the excess amine. Glacial acetic acid can also be used as a solvent in the chlorination step of this one-pot protocol, with subsequent distillation of acetyl chloride.[‌145‌] Equally good results are obtained when sulfuryl chloride is used as the chlorinating agent.[‌145‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeee Meeeee eee Meeeeeeeeeee ee Meeeeee Meeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee Meeeeeeeeeeeeeee (88, M8=M8=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee (MeM)8 (88.8e, 8.8eee) eee MeMM (88.8 e, 8.8eee) eee eeeeeee eee eeeeee ee 88°M eee Me8(e) (888.8e, 8.8eee) eee eeeee ee eeee e eeee eeee eee eeeeeeeeeee ee eee eeeeeee eee eeeeeeeeee ee 88 ee 88°M. Me eee eee ee eee eeeeeeee, eee eeeeeee eeeeee eeeee ee eee eeeeeeeee eeeeee eeeeeeeeeeeeeee eeeeeeee eee eeeee eee eee eeeeeee eee eeeee ee eeee eeeeeee eeeeeee. Meee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeee eeeeeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee e Meeeeee eeeeee ee eeeeee MMe eee MeMe. Meeee eeeeeee ee eee eeeeeee eeeeeeee, eee eeeee eeeeeee eee eeeeeeeeeee eeeeeee eeee MeMM (88eM, 8.88eee) eee eeee eeeeeeeee, eeeeeeeeee eee eeeeeeee eeee e eeeee ee 88°M ee eee ee ee eeeeee eeeeeeeeeeeeeeee (88°M/88Meee) ee eeeee eee eeeee eeeeeee (88e). Meee eeeee eeeeeee eee eeeeeee eeee ee eeeee eeeeee ee Me8M eee eeeeeee eeee e-eeeeeeeee (88e). Meeee eeeeeeee eee 88eee, eee eeeeeeeeeeee eeeee eeeeeeeeeeeee eee eeeeeee ee eeeeeee eeeeeeeeee eee eee Me8M eeee eee eeeee eeeeeee eeee e-eeeeeeeee (8e) eee eeeeeeee. Me8M eee eeee eeeeeee eeeee eeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee, eeeeeeee-eeee eeeeee; eeeee: 88.8e (88%); ee 8888°M/88Meee.

References