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39.11.3.1.2.4 Variation 4: Sulfurations Using Ammonium Thiocyanate or Thiourea in Reactions ­Catalyzed by Other Metal Salts

DOI: 10.1055/sos-SD-039-00701

Saito, M.; Nakayama, J.Science of Synthesis, (200839608.

In addition to cerium, ruthenium, and titanium salts, a variety of other metal salts are known to catalyze the conversion of oxiranes into thiiranes 69 (Scheme 24). Typical catalytic systems are summarized below. Thus, iron(III) trifluoroacetate (Method A),[‌76‌] [tetrakis(pentafluorophenyl)porphyrinato]iron(III) chloride (Method B),[‌77‌] and bismuth(III) chloride (Method C)[‌78‌] catalyze reactions that utilize ammonium thiocyanate as the sulfur donor. Acetonitrile at reflux is the usual solvent and under these conditions the reactions are normally complete within 1 hour or frequently less.[‌76‌‌79‌]

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Meeeeeeee 88; Meeeeee Meeeeeeee Meeee [Meeeeeee(eeeeeeeeeeeeeeeee)eeeeeeeeeeee]eeee(MMM) Meeeeeee:[‌88‌]

Meeeee M: MM8MMM (8.888e, 8eeee) eee Me(MM8MM)Me (8.888e, 8.88eeee) eeee eeeee ee eee eeeeeee (8eeee) ee MeMM (8eM) eee eee eeeeeee eee eeeeee eeeee eeeeee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeeeeee eeeeee eeeeeee e eeeee eeeeee ­(eeeeee eee, eeeeee/MeMMe 8:8) ee eeeeee eee eeeeeeee. Mee eeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeee.

Meeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeee(MMM) Meeeeeee:[‌88‌]

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Meeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeee(MMM) Meeeeee:[‌88‌]

M eeeeeee ee eee eeeeeee (8eeee), MMMM (8eeee), eee MeMe8 (8eee%) ee MeMM (88eM) eee eeeeeee ee 88°M. Meeee eee eeeeeeee eee eeee (MMM), eee eeeeeee eee eeeeeee eeee M8M eee eeeeeeeee eeee Me8M (8 × 88eM). Mee eeeeeeee eeeeeeee eeee eeeee (Me8MM8), eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8).

Meeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeee Meeeeeeeeeeeeeeee eee Meeeeeee Meeeeeeeeee ee eeee-Meeee Meeeeee:[‌88‌]

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Meeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeee Meeeeeeeeeeeeeeee eee Meeeeeee ee Meeeeeeeeeee:[‌88‌]

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Meeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee Meeeeeee Meeeeee:[‌88‌]

Meeeee M: MM8MMM ee eeeeeeee (8eeee) eee Me(MMM8)8 (8eeee) eeee eeeee ee eee eeeeeee (8eeee) ee MeMM (8eM) eee eee eeeeeee eee eeeeee eeeee eeeeee. Meeee eeeeeee ee eee eeeeeee, M8M (88eM) eee eeeee ee eee eeeeeee eee eee eeeeeee eee eeeeeeeee eeee MMMe8. Mee eeeeeee eee eeeee (MeMM8), eee eeeeeee eee eeeeeeeeee, eee eee eeeeeee eee eeeeeeeeeeeeeee ee e eeeee eeeeee (eeeeee eee, eeeeee/MeMMe 8:8).

Meeeeeeee 88; Meeeeee Meeeeeeee Meeee (Meeeeeeeeeeeeeeeeeeeeee)eee(MM) Meeeeeeeeeeee:[‌88‌]

Meeeee M: Meeeeeee (8.888e, 8eeee) eee Me(MMM)(MeM8)8 (8.888e, 8.88eeee) eeee eeeee ee eee eeeeeee (8eeee) ee MeMM (8eM) eee eee eeeeeee eee eeeeee ee eeeeee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeee eeeeeee e eeeee eeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeeeee eee eeeeeeee. Mee eeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeee eeeeeee, eeeee eee eeee eeeeeeeee.

References


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