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Please login to access the full content or check if you have access via Method 2: Synthesis from 1-Halo-1-(phenylsulfinyl)cyclopropanes via Carbenoid Intermediates

DOI: 10.1055/sos-SD-044-00163

Gandon, V.; Malacria, M.Science of Synthesis, (200844219.

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 sulfoxidemetal 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.

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Meeeeeeeeee 88

M8 M8 M8M Meeeeeeeee Meeee (%) Mee
888 888 888
8-MeMM8M8(MM8)8 Me MeMe ee e-MeMe 88°M, 8eee e e e [‌888‌]
8-MeMM8M8(MM8)8 Me MeMeMe 88°M, 8eee 8 8 88 [‌888‌]
8-MeMM8M8(MM8)8 Me eMeMeMe 88°M, 8eee 8 8 88 [‌888‌]
8-MeMM8M8(MM8)8 Me MeMeMe 88 ee 88°M, 8e, eeee 88°M, 8e 8 8 88 [‌888‌]
8-MeMM8M8(MM8)8 Me MeMeMe 8°M, 88eee 88 88 8 [‌888‌]
(MM8)8Me M MeMeMe 8°M, 88eee 88 8 8 [‌888‌]

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

M8 M8 M8 Meeee (%) Mee
(MM8)88 Me 88 [‌888‌]
(MM8)88 Me 88 [‌888‌]
(MM8)8 Me 88 [‌888‌]
(MM8)8 Me 88 [‌888‌]
Me (MM8)8Me Me 88 [‌888‌]

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

Meeeeeeeeee 88

M8M (eeeee) Meeeeeeeee Meeee (%) Mee
888 888 888
MeMeMe (8.8) 88 ee 8°M, eeee 8°M, 8.8e eeeee 88 8 [‌888‌]
MeMeMe (8.8) 88°Mee ee, eeee ee, 8.8e eeeee 88 8 [‌888‌]
eMeMeMe (8.8) 88°M ee ee, eeee ee, eeeeeeeee eeeee 88 8 [‌888‌]
e-MeMe (8.8) 88 ee 8°M, eeee 8°M, 8e eeeee 88 88 [‌888‌]
e-MeMe (8.8) 88°M ee ee, eeee ee, 8e 88 eeeee 88 [‌888‌]
e-MeMe (8.8) 88°M ee ee, eeee ee, 8e 88 88 88 [‌888‌]
e-MeMe (8.8) ee, 8e 88 88 88 [‌888‌]
Me8M(Me)MM (88) ee, eeeeeeeee 88 8 8 [‌888‌]

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 (88ee, 8.8eeee) ee eee MMM (8eM) eee eeeee ee 8M MeMeMe ee MMM (8.88eM, 8.8eeee) ee eee MMM (8eM) ee 8°M. Mee eeeeeee eee eeeeeee ee 8°M eee 88eee, 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: 88ee (88%); eee eee eeeeeeeeeeeee eeeeeeeeeeee 888 (ee 8:8) ee e eeeeeeeee eee; eeeee: 8.8ee (88%).

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

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