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. Variation 1: By Using Hydrogen Sulfide and Acid

DOI: 10.1055/sos-SD-027-00185

Collier, S. J.Science of Synthesis, (200427180.

Early syntheses of thioaldehydes, first pursued in the nineteenth century, involved the treatment of aldehydes with hydrogen sulfide under acidic conditions. Detailed reviews of this early work have been published, and include observations on the preparation of thioformaldehyde and thioacetaldehyde by using this technique.[‌1‌,‌3‌] The unstable thioaldehydes thus produced are often obtained as cyclic trimers or as polymers[‌37‌‌39‌] and, in some cases, yields of the trimers are very high. The use of basic media promotes polymerization and disproportionation of arylthioaldehydes to form benzyl thiols and dithiobenzoic acids by the Cannizarro reaction.[‌37‌]

Mee eeeeeee 88 eee eeeee ee eee eeeee, eee α- ee eeeee-eeee eee eee β- ee eee-eeee, eee eeeee ee eeeee eeeeeee eeee eee eeee ee eee eeee eeeeee (Meeeee 8). Meee eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeeeeeee, eeee eeeeeee eee eeeeeeee ee e eeeee eeee eeeeeee eeee eee eeee ee eee eeee eeeee. Mee eeee eeeeeeee eeeeeeee eeeeee eeeee eee eeeee-eeeeee eeeeeeeeeee, eeeeeee eee eeeeee eeeeeeee eeeeeeeeee eeeeeeee eeeee eeee eeeeeeee, eeeeeeeeee eeeeeee ee eee eeeeee eeeeeeeeee eeeeeeeeee eeee eeeeeeeeeeeee. Meeeeeeeee eee eeeeee eeee eeee eeeeeee ee e eeeeeeeeeee eeeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeee; eeeeee eeeeeeeee ee eeeeeeeeeee-8-eeeeeeeeeeeeeeee eee 8-eeeeee-eeeeeeeeeee-8-eeeeeeeeeeeeeeee eeeeee eeeeeeee eeeeeeeeeeeeee eee 88 eeee.[‌88‌] Meeeeeeeeeee ee eee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee eeee eeeeee eeeeeeeeeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeee, eeeee eeee eeee eeeeeeeee, eeeeeeeee eeeeeeeee ee eeeeeeeee eee eeeeeeeeee. Me eee eeeeeee ee eeee ee ee eee eeeeeeee ee eeeeee eeeeee, eeeeeeee eeeeeeeee eee eeeee ee eeee eeeee.[‌88‌,‌88‌] Meee eeeeeeee eee eeee eeee eeee ee eeeeeee 8,8-eeeeeeeeeeeeeeeeeeeeeeeee.[‌88‌] M eeeeeeeeeeee ee eeee eeeeeeee, eeeeeeeee eeeeeeeee ee eee eeeeeeee eeee eeeeeeee eeeeeee ee eee eeeeeeee ee eeeeeeee eeeeeeeeeeee eee e eeeeeeeee eeeeee ee eeee(MM) eeeeeeee, eee eeee eeee ee eeeeeee eeee-8-eeeeeeee eeee eeeeeeee, eeeeeeee eeeeee eee eeeee eee.[‌88‌]

Meee eeeeeeeeeee eee eeee eeeeeeeeee ee e eeeee eeeeee ee eeeeee eee eeee eeeeeeeee eeeeeeee, eeeeeee ee eeeee eee eeeee ee Meeeeeee eee

Meeeee 8 Meeeeeeeeee ee Meeeeeeeeeeee eeee Meeeeeeee eee Meeeeeee Meeeeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 8

Me8 Meeee (eeeee-88/eee-88) Meeee (%) ee 88 Mee
8-MeM8M8 88:88 88.8 [‌88‌]
8-MeM8M8 88:88 88.8 [‌88‌]
8-MeM8M8 88:88 88.8e [‌88‌]
8-MeM8M8 88:88 88.8 [‌88‌]
8-MeM8M8 88:88 88.8 [‌88‌]
8-MeM8M8 88:88 88.8 [‌88‌]
8-MM8M8 88:8 88.8 [‌88‌]
8-MM8M8 88:8 88.8 [‌88‌]
8-MM8M8 88:8 88.8 [‌88‌]
888:8 888e [‌88‌]
88e [‌88‌]

e MeMM (88eM) eeeee ee MeMMe ee eee eeeeeeeeeee.

e Meeeeeee eeeeeeeeee: eeeeeee eeee ee eeeeeeeee.

e Meeeeeee ee eee eeeeeeeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeee eeee Meeeeeeee eee Meeeeeee Meeeeee; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeee eeeeeee ee eeeeeeeee eeeeeeeee eee ee eeeeee eeeeee eeeeee eeeeeeeeeee eeeeeeeee eee eeeeeeee.

Mee eeeeeeeeeeee eeeeeeeeee (88eM ee e eeeeee, 8e ee e eeeee) eee eeeeeeeee ee MeMMe (888eM) eee eeeeee ee 8°M. MMe(e) eee eeeeeee eeeeeee eee eeee eeeee eeeeeeeeee eee eeeeeee, ee eeeee eeeee M8M(e) eee eeee eeeeeee eeeeeee eee eeeeeee. MMe(e) eee eeeee ee e eeeeee eeee eeee M8M(e) eeeeeeeeee eee eeeeeeee ee eee eeeeeeee. Meeee 8e, eee eee eeeeeeee eee eeeeeee eee eee eeeeeeee eee eeee ee eeeee eeeeeeeee eeee eeeeeee ee eeee ee ee. Mee eeeeeeeee eeeeeeeeeee eee eeeeeeee eee. Mee eeeeeeee eee eeeeeeeee ee eee eeeeeeee eeeeeeeeee eeeee eee eeeeeee ee eeeee eee 8e ee eeee e eeeeee eeee ee eeeeeeee. Mee eeeeeeee eeeeeee eeeeeeeee eeee eeeeeeeeeeeeee [eeeeeee (MMMMMMM: eeeeeeeeee) ee MeMMe] ee eeee eee eeeeeeeeeee eeeeeeeeeeeeeeee eeeeee.