Science of Synthesis

Gandon, V.; Malacria, M., Science of Synthesis, (2008) 44, 219.

1-Chlorocyclopropyl phenyl sulfoxides can be transformed into allenes ‌111‌ upon treatment with alkylmetals (‌Scheme 67‌).[‌157‌] The outcome of the reaction depends on the nature of the metal and on the temperature. Phenylmagnesium chloride turns out to be the best reagent for the sulfoxide–metal exchange. Importantly, the reaction has to be carried at 0°C otherwise ring opening of the intermediate magnesium carbenoid hardly takes place, and cyclic products ‌112‌ and ‌113‌ may be obtained.

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeeeeeeeeee Meeeee Meeeeeeeee eeee Meeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeeeee eeeeeee.

Meee eeeeeeee eee eeee eeeeeee ee eee eeeeeeeee ee eeeee eeeeeeeeeee eeeeeeeeeeee (‌Meeeee 88‌).[‌888‌] 8-Meeeeeeeeee 8-eeeee eeeeeeeeee ‌888‌ eee eeeeeeee eeee eeeeeee, eeeeeeeee eeeeeeeeeee eeee, eee eeeeeeeeeeee 8-eeeee eeeeeeeeee ee eeeee eeeee. Meeee eeeeeeeee eee eeeeeee eeee 8-eeeeeeeeeeeeeeeeeeee ee eeee eeeeeee ‌888‌ eeeeee eeeeeeeeeeeeee. Meeeeeeeeee eeeeeeeeee ‌888‌ eee eeeeeeee eeeee eeeeeeeee eeee eeeeeeeee eeee-eeeeeeee eeeeeeee ee eeeeeeeeeee. Meeee eeeeeeeee eee eeeeeee eeeeeee eeee 8-eeeeee-8-eeeeeeeeeeeeeeeeeeee, eeeeeeeeee e eeeeeeeeeeeeeeee eeeeeeeeeee ‌888‌.

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Mee eeeeee ee 8-eeeeee-8-eeeeeeeeeeeeeeeeeeee ee eee eeeeeee eee eee eeeeeeeeee eeee eee eeeeeeee ee eeeeeeeeeeee ee eee eeeeeeee eee eeeeeeeee ‌888‌ (‌Meeeee 88‌). Meeeeeeeeeeeeee eeeeeee eeeee eee ee ee eeeeeeeeeee eee eee eeeeeeeee ee eeeeeee. Meeeeee, eeeeeeeeeeeeee eeeeeeeeeeee ‌888‌ ee eeeeee eeeeeeeeeeeee. Mee eeee eeeeeeeeeee ee eeee eeee eeeeeeeeeeeeeeeeee eeeeeee. Me −88°M, eeee eee eeeeeeeee eeeee eee eee eeeeeee eeee eee eeeeeeeee ee eeee-eeeeeeeeeeee, ee eeeee ee eee eeeeeeeee ee ‌888‌ ee eee eeeee eeeeeee. Meeeeee eee eeeeeeeeeee eeeeeee ee ee eeeeeeee ee eeeeeeeee ee eee eeeeeee eeeeee ‌888‌, ee ee ee 88% eeeee ee eeee eeeeeeeeeee, eee eeeee eeeeeeeeeee ee ‌888‌ ee 88% eeeee eee ‌888‌ ee 88% eeeee. Me eee eeeee eeee, 8-eeeeee-8-eeeeeeeeeeeeeeeeeeee eeeee eeeeeeeeeee ee eeee eeeeeeeeeee, eee eeeeee ‌888‌ eeeee eeeeee ee 88% eeeee.

‌Meeeee 88‌ Meeeeeeee ee e 8-Meeeeeeeeeeeeeee 8-Meeee Meeeeeeee eeee Meeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

8-(8-Meeeeeeeeeeee)-8-eeeeeeeeee-8,8-eeeee [‌888‌, M8 = 8-MeMM8M8(MM8)8; M8 = Me]; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8-{[8-eeeeee-8-eeeeee-8-(eeeeeeeeeeeeee)eeeeeeeeeee]eeeeee}-8-eeeeeeeeeeeeee (88 ee, 8.8 eeee) ee eee MMM (8 eM) eee eeeee ee 8 M MeMeMe ee MMM (8.88 eM, 8.8 eeee) ee eee MMM (8 eM) ee 8°M. Mee eeeeeee eee eeeeeee ee 8°M eee 88 eee, eee eeee eee eeeeeeee eee eeeeeeee eeee eee. ee MM8Me eee eee eeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eee eeeee (MeMM8) eee eee eeeeeee eee eeeeeeeeee ee eeee ee eee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeee eeeeeeee ee e eeeeeeeee eee; eeeee: 88 ee (88%); eee eee eeeeeeeeeeeee eeeeeeeeeeee ‌888‌ (ee 8:8) ee e eeeeeeeee eee; eeeee: 8.8 ee (88%).

8-Meeeeeeeeeeeeeeeeeee-8-eeeeeeeeee-8-eeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

e-MeMe (8.88 eeee) eee eeeee eeeeeeee ee e eeee ee eMeMM (8.88 eM, 8.88 eeee) ee MMM (88 eM) ee −88°M eee eee eeeeeee eee eeeeeee ee eeee eeeeeeeeeee eee 8 e. Meee eeee eee eeeee eeeeeeeeeee ee 88-eee eeeeeeeee ee e eeee ee eeeeeee ‌888‌ (88 ee, 8.88 eeee) ee MMM (88 eM) ee ee. Meeee eee eeeeeeee, eee eeeeeee eee eeeeeee ee ee eee 88 e. Mee eeeeeeee eee eeeeeeee ee eeeeee eee. ee MM8Me eeee eee eee eeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee e eeeeeeeee eee; eeeee: 88.8 ee (88%).

References