Science of Synthesis

Segi, M., Science of Synthesis, (2008) 39, 833.

Cyclic dialkyl sulfides can be prepared via cyclization by the alkylation of metal sulfides (metal salts of hydrogen sulfide) with alkyl dihalides. Sodium sulfide nonahydrate ­(Na2S•9H2O) is commercially available and well used in this approach to the synthesis of cyclic sulfides. Some thiabicyclooctanes may be synthesized in moderate yields by the reaction of dibromides with sodium sulfide.[‌8‌] The thiosugar derivative ‌2‌ is prepared at 100°C in dimethylformamide by the alkylation of sodium sulfide with the corresponding dibromide, which is obtained from the D-ribose-derived alcohol ‌1‌ (‌Scheme 1‌).[‌9‌]

‌Meeeee 8‌ Meeeeeeeeee ee e Meeeeeeee Meeeeeeeee ee eee Meeeeeee ee e Meeeeeeee eeee Meeeee Meeeeee[‌8‌]

Meeeeeeeeee eeeeeeeee eeeeeeee ‌8‌ eee eeeeeeee ee eeeeeeeeee eeeeee ee eeeeeeee ee eeeee(eeeeeeee eeeeee) eeeeeeeeee eeee eeeeee-8,8-eeeeeee, eeeeeee-8,8-eeeeeee, ee 8,8-eeeeeeeeeeeeeeee-8-ee ee eeee eeeeeeee ee eeeeeee eeeeeeee ee eeeeee eeeeeeeee (‌Meeeee 8‌).[‌88‌] Meeeeee eeee-eeeee eeeeeeeee eee eeeeeeee ee eee eeeeeeee ee 8,8′-eeeeeeeeeeeeeeeeeeeeeeee (8-eeeeeeeeeee-8,8-eeeeeee) eeee eeeeeeeeeee eeeeeee eeeeeeeeee ee 8–88% eeeeee, eeeee e eeeeeeeeee eeeeeeee eeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeee ee Meeeeeeeeee Meeeeeeee Meeeeeee ee eee Meeeeeeee ee Meeeeeeeeee eeee Meeeeeee ee eee Meeeeeee ee Meeeee Meeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeee-8,8,8-eeee-M-(8-eeeeeeeeeeeee)-8-eeee-M-eeeeeee (‌8‌); Meeeeee Meeeeeeee:[‌8‌]

Me e eeee ee 8,8,8-eeee-M-(8-eeeeeeeeeeeee)-M-eeeeeee (‌8‌; 888 e, 8.88 eee) ee eeeee eeeeeeee (888 eM) eee eeeee MeMe (888 eM, 8.8 eee) ee 8°M. Meeee eeeeeeee eee 88 eee, eee eeeeeeee eee eeeeeeee eeee eee eee eeeeeeeeeee eeeeeee MeMMe eee M8M. Mee eeeeeee eeeee eee eeeeee eeee eee. ee MeMMM8 (8 ×) eee eeeee, eeee eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeee eeeeeee eeeee eeee eeeeeee. Mee eeeee eeeeeeeeeeeeeeee eee eeeeeeeee ee MMM (8 M), eee MeMe (888 e, 8.8 eee) eee eeeee, eee eee eeeeeee eee eeeeeeee eee 88 e. Meeee eeeee eeeeee ee ee, eee eeeeeee eee eeeeeee eeee MeMMe, eee eeeeee eeee M8M eee eeee eeeee. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeeeee. Mee eeeeeeeee eee eeeeeeeee ee MMM (8 M), eee Me8M•8M8M (88.8 e, 8.88 eee) eee eeeee ee eee eeee. Mee eeeeeee eee eeeeee ee 888°M eee 88 eee. Meeee eeeee eeeeee ee ee, eee eeeeeee eee eeeeeee eeee MeMMe eee eeeeee eeee M8M (8 ×), eeeeeeee ee eeeee. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8 ee 8:8) ee eeee e 8:8 eeeeeee ee ‌8‌ eee eee eeeeee; eeeee: 888.8 e (88%). Meeeeeeeeeeeeee (eeeeee/MeMMe) eeee eeeee eeeeeeee ee ‌8‌; 88.8 e (88%); ee 88°M.

8,8,8,88-Meeeeeee-88,88-eeeeeeeeeeeeeeeeeeeee (‌8‌, M8 = M; e = 8; e = 8); Meeeeee Meeeeeeee:[‌88‌]

8,88-Meeeeeee-8,8,8,88-eeeeeeeeeeeeeeeeeee (88 e, 8.888 eee) eee eeeeeee-8,8-eeeeeee (8.8 e, 8.888 eee) eeee eeeee eeee eee MeMM (888 eM) eee eeeee eeeeee ee e eeeeeee eeee ee ee eeeeee ee MeMM ee eee MeMM (888 eM). Mee eeeeeeee eeeeeeee 88 e ee eeeeeee. Meee ee eee eeeeeee (8 e) eee eeeeeeee ee eeeeeeeeeeeeee [eeeeeee (88 e; eeeeee eeee MeMMe eee eeeee ee 888°M eee 88 e), eeeeee/MMMe8 8:8, 8:8, 8:8, 8:8, 8:8, 8:8 (888 eM eeee) eeee MMMe8 (888 eM)]. Mee eeeeeee eee eeeeeeee ee e eeeeeee eee eeee eee 8:8 eeeeee/MMMe8 eeeeeeee; eeeee: 8.88 e (88%); Me 8.88.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 888.