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39.13.4.1.2.1.15 Methods 15: Miscellaneous Methods

DOI: 10.1055/sos-SD-039-00950

García-Ruano, J. L.; Cid, M. B.; Martín-Castro, A. M.; Alemán, J.Science of Synthesis, (200839779.

The addition of 2-methylpropane-2-sulfenic acid (obtained by thermolysis of di-tert-butyl sulfoxide) to alk-1-enes affords tert-butyl 1-methylalkyl sulfoxides in good yields. The method has found a second general application in the synthesis of four- to seven-membered ring sulfoxides, e.g. 37, when the sulfenic acid moieties are added intramolecularly to CC multiple bonds.[‌204‌,‌205‌] The method is also applicable to cyclic dienes[‌204‌,‌205‌] (Scheme 27).

Meeeee 88 Meeeeeeeeee ee Meeeee Meeeeeeeee ee Meeee- eee Meeeeeeeeeeeee Meeeeeee ee Meeeeeee Meeee ee Meeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 e Meeeeeeeee Meeeee (%) Mee
88M 88M 88M
M 8 888°M, 8.8e 88 8 e [‌888‌]
M 8 888°M, 8e 8 88 e [‌888‌]
Me 8 888°M 88 88 8 [‌888‌]
M 8 888°M, 8.8e 88 8 e [‌888‌]

e Mee eeeeeeeeee eeeee eeeeeeee eeeeeeee eeeeeeeeeeeeeee.

e Meee M8=M, 88M=88M.

8-(Meeeeeeeeeeee)-8-[(8-eeeeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeeee 8-eeeeee (eeeeeeee eeeeeeeeeee) eee ee eeeeeeee eeeeeeeeeeeeeeeee eeee eee eeeeeeeeeeeee eeee-eeeee eeeeeeeeee eeeeeeeee eee eeee eeeeeeee (Meeeee 88).[‌888‌] Meeeeeeee eeeeeeeee ee 8-eeeee-8-(eeeeeeeeeeeee)eeeeeeee 8-eeeeee eeee eeee eeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeee ee Meeeeeee Meeeeeeeeee ee Meeeeeeeeeeeee Meeeeeee ee Meeeeeee Meeee ee Meeeeee[‌888‌]

Meeeeeeeeee ee eeeeee eeeeeeeeee eeeee eeeee, eee eeee-eeeee eeeeeeee eeeee, ee eee eeeeeeee eeeeeeeeee. Mee eeeeeeeeee eeeeeeeee eeeeeeee, eee eeeeeee, eee eeeeeeeee ee eee-8-eeeeee- eee eee-8-eeeeeeeeeeeeeeeeeeeeeeee 8-eeeeee eeee eeeeeeee 8-eeeee eee eee-8-eeeeeeeeeeeeee 8-eeeee, eeeeeeeeeeee, ee 888°M ee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meee Meeeeeeeeee ee Meeeee Meeeeeeeee ee Meeeeeeeeee[‌888‌]

Meeeeeee eeee 8,8,8,8-eeeeeeeeeee-8-eeeeeeeeeee 8-eeeee (88), 8-eeeeeee-8,8,8-eeeeeeeeeeeeeeeeeeeeeeee-8(8M)-eee (88) ee eeeeeeee eee eee eeeeeeeeeeee eeee-eeeee eeeeeeee eeee, eeeee eeee 8,8,8-eeeeeeeeeeeeeeeeeeeeeeee-8(8M)-eee 8-eeeee (88) ee e eeeeeee ee eee- eee eeeee-eeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meee Meeeeeeeeee ee Meeeee Meeeeeeeee ee Meeeeeeeeee[‌888‌]

Mee eeeeeeee eeeeeeeeeee/eeeeeeeeeeeeee eeeeeeee[‌888‌,‌888‌] ee eeeeeeeeee eeeeeeeeee eeeeeeee eeeee eeeeee eeeeeeeee ee eeee eeeeeeeeeeeeee; ee eeeee eeeeeee e eeeeeeee (ee eeeeeee ee e-MeMM ee eeeeee) eeee eee M-eeeeeeeeee ee eee M-eeeeeee.[‌888‌‌888‌] Mee eeeeeeee eeeeeeeee eeee ee eeee eeeeeeee eeee ee eeee eee eeeeeeee eeee[‌888‌] ee eeee eee eee eeeeeeeee ee eeee eeeeeeeeee eeeeeee eeee eeeeeeeeee,[‌888‌] eee eeeeeee eeeeeeee eeee eeeeeeeeee[‌888‌‌888‌] ee eeeeeee.

Meeeeeeeeeeee M-eeeeee eee ee eeeeeeee eeee eeeeeeee eeeeeeeee eeee eeeeeee eeee eeeeeeeeeeeee (88°M, 8eee ee MM8Me8 ee eeeeeee). Me eeee, eeeeeeee eeeeeeeee eee eeeeeeeee eeee eeeeeeeeee M-eeeeee eeeeeee eeeeeeeeeee ee eeeeee eeeeeeeeeeeee ee eeeeee ee eee eeeeeeee ee ee eeeeeeeee eeeeee ee eeeeeeee eeeeeeee[‌888‌] (Meeeee 88).

Meeeee 88 Meeeeeeeeee ee Meeeeeeeee M-Meeeee Meeeeee ee Meeeeeeeeeeee M-Meeeee[‌888‌]

Meee(eeeeeeeeeee eeeeeeeee) ee eeeeeeee ee eeeeeeeeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeee eeee eeeeee eeeeeeee(MM) eeeeeeeeeeeeeeeeeeeee eeeeeeeeee, eeeeeeeeee(M) eeeeeeee, ee eeeeeeeee(MM) eeeeeeee eeeeeeeee[‌888‌] (Meeeee 88).

Meeeee 88 Meeeeeeee Meeeeeeeeeeeeeeeeee ee Meeeeeeeeee Meeeeeeee[‌888‌]

Mee eeeeeeeeee ee eeeeeeeeeeeeeeeeee eeeee ee eeeeeeeee eeeeee ee e eeeeeeeee eeeeee, ee eee eeeee eee eeeeeeee ee eeeeeeeeee ee eee eeeeeeeeee; eeeeeee, eee eeeeeeee eee eeeeeeeeeeee eeeeeee ee eee eeeeee eeeeee. Meeeeeee eee eeeeeeeeeeeeee eeeeee ee e eeeeeeeeeeee eeeeeeeeeeee ee eee eeeeee eeee eeee eeeeeeeee ee eeeeeeeeeeeee, ee eee eeee eeeee ee eee eeeeeeeeee ee eeeeee eee-[‌888‌,‌888‌] ee eeee-eeeeeeee eeee eeeeeeeeeee,[‌888‌] ee eeeeeeee eeeeeeeeeeee eeeee.[‌888‌]

Me eeee eeeeeee eee eee eeeeeeeee ee eeeeeeee ee eeeeeeeeee, eeeeeeeeeeeeeee eeeee eee ee eeeeeee ee ee eeeeeeeeeeeee. Meeee eeeeeeeeeeeee eee ee eeeeeeee ee eeeeeee eeeee eeee ee eeeeee eee-eeeeeeeee eeeee 88, eeeee eee ee eeeeeeee ee eeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeee Mee-eeeeeeeee Meeee eee Meeee Meeeeeeeeeeeee eeee Meeeeeeeee[‌888‌]

References


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