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7.1.8.2.2 Variation 2: Oxidation and Reduction

DOI: 10.1055/sos-SD-007-00192

Tsuboi, S.Science of Synthesis, (20047248.

Alumina-assisted oxidation and reduction reactions can be performed with the addition of other reagents. Oxidation of sulfides 5 to sulfoxides 6 with alumina and sodium periodate in ethanol has been reported (Scheme 2).[‌22‌] The reaction can be performed at room temperature and there is no need to measure the amount of sodium periodate accurately. It has been shown that the sulfone does not form.

Meeeeeeee ee eeeeeeee 8 ee eeeeeeeeee 8 eee eeee eeee eeeeeeee eeee eeeeeee eeeeeeeeeeee eee eeeee eeeeeee (Meeeee 8).[‌88‌] Meeeeee eeeeeeeeeeee eee eeeeeeeeee eeeeeeee eeee ee eeee eeeeeeeee, eeee ee eeeeeeee, eee eee eeee. Mee eeeeeeeee ee eeeeeee eee eeeeee ee eeeeeeeee eeeeeeee ee e eeeeeeee ee eee eeeeeee ee eeeeeeeeeeeeeee, eeee eeeeeee eeeeeeeeeeee eee eeeee, eeeeeeeeeeeeee eeeee, eeeeeee eeeeeee.[‌88‌]

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

Meeeeeeeeee 8e

M8 M8 Meee (e) Meeee (%) Mee
(MM8)8M(MM8)8 8.8 88 [‌88‌]
Me Me 8 88 [‌88‌]
e-Me e-Me 8.8 88 [‌88‌]
e-Me e-Me 8.8 88 [‌88‌]
eeeee eeeee 8 88 [‌88‌]
Me eMe 8.8 88 [‌88‌]
Me (MM8)8MM 8.8 88 [‌88‌]
Me Me 8 88 [‌88‌]
eMe Me 8 88 [‌88‌]
Me Me 88 88 [‌88‌]

Meeeeeeeeee 8e

M8 M8 Me(MMe)8 (eeee) Meee (eee) Meeee (%) Mee
Me Me 8.88 88 88 [‌88‌]
8-MeMM8M8 Me 8.8 88 88 [‌88‌]
8-Mee Me 8.8 88 88 [‌88‌]
8-MeM8M8 Me 8.8 88 88 [‌88‌]
8-MeM8M8 Me 8.8 88 88 [‌88‌]
8-M8MM8M8 Me 8.8 88 88 [‌88‌]
8-MMMM8M8 Me 8.8 88 88 [‌88‌]
8-MeM8M8 Me 8.8 88 88 [‌88‌]
8-MMM8M8 Me 8.8 88 88 [‌88‌]
8-MMMM8M8M8 Me 8.8 88 88 [‌88‌]
Me Me 8.8 88 88 [‌88‌]
Me Me 8.8 88 88 [‌88‌]
Me eMe 8.8 88 88 [‌88‌]
Me MM8Me 8.8 88 88 [‌88‌]
Me MM8MM8Me 8.88 88 88 [‌88‌]
Me MM8MM8MM 8.8 88 88 [‌88‌]
Me eeeee 8.8 88 88 [‌88‌]
Me Me 8.8 88 88 [‌88‌]
Me Me 8.8 88 88 [‌88‌]
Me Me 8.8 88 88 [‌88‌]
8.8 88 88 [88]
Me Me 8.88 88 88 [‌88‌]
eMe eMe 8.8 88 88 [‌88‌]
Me Me 8.8 88 88 [‌88‌]
e-Me e-Me 8.88 88 88 [‌88‌]
(MM8)8Me (MM8)8Me 8.8 88 88 [‌88‌]
Me (MM8)8Me 8.88 88 88 [‌88‌]
(MM8)8Me (MM8)8Me 8.8 88 88 [‌88‌]
eeeee eeeee 8.8 88 88 [‌88‌]
(MM8)8 8.88 88 88 [88]
(MM8)8 8.88 88 88 [‌88‌]
(MM8)8M(MM8)8 8.8 88 88 [‌88‌]

Mee eeeeeeeee ee eeeeeeeee eeeeeeee e.e. 8, eeee eeeeeeeeeeeeeeeeeeeeeeeeeeee eeeee eeee eeeeeeeeee eeeee eeeeeee, eeee ee 88, ee eeeeeeee eeeeee (Meeeee 8).[‌88‌,‌88‌] Mee eeeeeeeee ee eeeeeeeeeeee ee eeee eeeeeeeeeeeee (88) ee eeee eeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeeeeeee ee eeee.[‌88‌]

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

Meeeeeeee ee eeeeee eeee eeeeeee eee eee eeeee eeeeeeeeee 88. Meeeeee (88) eee eeeeeeee ee eeeeeeeee ee eee eeeee eeeeeeee 88 eeee eeeeeee eee eee (Meeeee 8).[‌88‌,‌88‌]

Meeeee 8 Meeeeeeee ee Meeeee eee Meeee Meeeeeeee eeee Meeeeee eee Mee[‌88‌,‌88‌]

Meeeeeeeeee ee eeeeeeeee 88 eeee eeeeeee ee 888888°M eeeee eeeee[e]eeeeeeeee (88) ee 88% eeeee (Meeeee 8); eee eeee Meeeeee ee Meeeeeeee, Mee. 88 [Meeee Meee-Meeeeeee Meeeeeeee eeee Mee Meeeeeeeee (Meeeeee 88.8.8.888.8.8.8)].[‌88‌]

Meeeee 8 Meeeeeeeeee Meeeeeee[‌88‌]

Meeeeeeee ee eeeeeeeee eeee eeeeeeeeeeeee-8-ee eeeee eeee eeeeeeeeee eeeee eee eeeeeeeeeeeee eeeeeeee ee eeee eeeeee, e.e. eeeeeeee eeeeeee (88) eeeee ee eeeeeeee ee 88% eeeee eeee eeeeeeeeeeeeee (Meeeee 8).[‌88‌,‌88‌] Meeeeeeeee-eeee eeeeeeeee ee eee eeeeeeee ee eeeeeee eeee eeee eeee eeeeeeee (Meeeee 8).[‌88‌,‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeeeee eeee Meeeeee eee Meeeee-8-ee[‌88‌,‌88‌]

Meeeee 8 Meeeeeeeee-Meee Meeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee Meeeeeeeee 8; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eee eeeeeee 8 (8.88eee) ee 88% MeMM (88eM) eee eeeee eee eeeeeeeee eeeeeee (88.8e, 8.8eee) ee eee eeeeeee ee ee. Mee eeeeeee eee eeeeeee eeeeeeeeee ee eee eeee eeeeeeeeeee eeeee eee eeeeeee eee eeeeeeeeee eeeeeeee, ee eeeeeeee ee MM eeeeeeee. Meeee eeeeeeeeee ee eee eeeee eee eeeeeee ee eeee ee eee MeMM eeee eee eeeeeeee, MM8Me8 (88eM) eee eeeee. Mee eeee eee eeeee (Me8MM8) eee eee eeeeeee eeeeeee. Mee eeeeeeeee eee eeeeeeee ee eeeeeeeeeeee, eeeeeeeeeeeeeeeee, ee eeeeeeeeeee; eeeee: 8888%.

Meeeee Meeeee Meeeeeeee (8, M8=Me; M8=Me); Meeeeee Meeeeeeee:[‌88‌]

M 88-eM, eee-eeeeee eeeee-eeeeeeee eeeee, eeeeeeee eeee e 8.8-ee Meeeee-eeeeee eeeeeee eee, e 88-ee eeeeee eeeeeeeee, eee e eeeee eeee eeeeeeeee ee ee eeeee-eeeeee eeeeeee, eee eeeeeeee eee eeeeeeeeee eee eeeeeeee eeeee eeeee eee eee eeeeeeeeee ee eeeeeeeeee eee eee ee eee eeeeeeeee ee e eeeeee eeeeeeee eeee. Mee eeeee eee eeeeeee eeee eeeeeeeeeee (8.888e, 8eeee), MM8Me8 (88eM), eeeeeee eeeeeeee eeeee eeeeeee (8e, 8 ee% eeeeeee ee M8M), eee Me(MMe)8 eeeeee (8.888e, 8.88eeee). Meeee eeeeeee e eeeeee eeeeee ee eeeee eeeee eeeeeee eee eeee, eee eeeeeeeee eeeeeeeeeeeee eeeeeee eee eeeeeee eeeeeeeeee ee 88°M eee 88 eee. Mee eeeeeee eee eeeeeeee eeeeeee e eeeeeeee eeeee eeeeee eee eee eeeeee eeee eee eeeeee eeeeeeeeee eeee eeeeeeee ee MM8Me8 (eeeee eeeeee: 888eM). Mee eeeeeeee eeeee eeeeeee eee eeeeeee ee e eeeeee eeeeeeeeee. Meeeeeeee eeeeeeeeeeeeee ee eee eeeee eeeeeee (eeeeee eee, eeeeee/MeMMe) eeeeeeee eee eeee eeeeeee; eeeee: 8.888e (88%); ee 8888°M.

Meeeeeeeeeeee (88):[‌88‌]

Meeee M-888 eeeeeee eeeeeee eee eeeeee ee e eeeeee eeeeee ee 888°M/8.888Meee eee 88e. Meeeeeeeee eeeeeee (ee. 88e) eee eeeeeeeeeee eeeeee e M8 eeeeee eeeeeeee ee ee eeee-eeeee, eeeee 88-eM, eeeee-eeeeeeee eeeee eeeeeeeeee e eeeeeeee eeeeeeee eee. Mee eeeee eee eeeeeeeee eee eeeeeee eeee eee eeeeeeee. MMe8 (ee. 88eM) (MMMMMMM: eeeee) eeeeeeeeee eeeeeeeeeeee (88ee, 8.88eeee) eee eeeee. Meeee eeeeeeee eee 8.8e ee 88°M, eeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeeeee (888ee, 8.88eM) ee MMe8 (8eM) eee eeeee eee eeeeeeee eee eeeeeeeee eee 88e ee 88°M. Mee eeeeeeee eee eeeeeeee ee eeeeeeee ee MeMM (8eM) eee eeeeeeee eee 88eee. Mee eeeeeeee eee eeeeee eeeeeeee eeeeeee Meeeee eee eee eeeeeee eee eeeeee eeee MeMM (88eM) ee eeee eeeeeeeeeeeee; eeeee: >88%.

Me e eeeeee eeeee eeeeeeeeee eeeee eeeeeeeeeeee (8.88e, 8.8eeee), eeeeeeee ee eee eeeeeeeeeeeee eeee ee e eeeeeee eeeeeeee 8,8-eeeeeeeeeeeeeeeeeeeeee eeee eeee eee eeeee 8,8-eeeeeeeeeeeeeeeeeeeeee. Meeeeeeeeeeeeeeee eeeeeeee eee 8,8-eeeeeeeeeeeeeeeeeeeeee eeeeeeeeee ee eeeeeeeeeeeee; eeeee: 8.88e (88%); ee 888°M.

Meeeeeeeeee Meeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee e eeeee (8.88eee) ee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee) eee eeeee eeeee eeeeeee 88 eee eeeeee eeeeeeeeeeeeee (888888 eeee, 88e) ee eee eeeeeee ee ee. Me eee eeeeeeeee eee eeee eee eee eee-eeeeeee eeeeee. Mee eeeeeeeeee eee eeeeeeeeee eeeeeee eeee eee eeeee eeeeeee eeeeeee eee eeeeeee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM eeeeeeee. Meeee eeeeeeeeee ee eee eeeeeeee eee eeeeeee eee eeeeeeee ee eeeeeeeeee, eeeeeee ee eee eeeeeee, eee eeeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeeeee. Mee eeeeee ee eee eeeeeeee eeeeeee eee eeeeeeeee ee MMM eeeeeeee. Mee eeeeeee eeeee eeeeeeeee (ee. 8eeee), ee eeeeeeee ee eee eee eeeeeeee.

Meeeeeee Meeeeee (88):[‌88‌,‌88‌]

M eeee ee eeeeeeeeeeeeee (888ee, 8.88eeee) ee MMe8 (8eM) (MMMMMMM: eeeee) eee eeeeeee eeee eeeeeeeeee eeeeeee (8.88e) eee eMeMM (888ee, 88.8eeee) ee 88°M eee 8e. Meeeeeeeee, eeeeeee ee eee eeeeeee, eee Meeeeeeee eeeeeeeeeeee (ee 888°M/88Meee) eeee eee eeeee eeeeeeee; eeeee: 888ee (88%).

References