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Please login to access the full content or check if you have access via Method 10: Oxidation with Dimethyl Sulfoxide

DOI: 10.1055/sos-SD-026-00003

von Angerer, S.Science of Synthesis, (20052689.

Oxidation with activated dimethyl sulfoxide effects a mild and general conversion of alcohols into aldehydes and ketones, respectively.[‌319‌] A variety of different reaction conditions are commonly used and they share the virtues of ease of operation, formation of products in high yield, the absence of major side reactions, including racemization and overoxidation, simplicity of product isolation, and compatibility with a wide range of other functional groups. The conditions are adaptable to both large and small scale operations. A common intermediate in the various procedures is the alkoxysulfonium salt 114 (Scheme 76), derived from dimethyl sulfoxide and the alcohol by treatment with an electrophile such as oxalyl chloride (Table 9, entries 1 and 2),[‌320‌‌323‌] 4-tolu­enesulfonyl chloride,[‌324‌] trichloromethyl chloroformate (Table 9, entry 3),[‌325‌] phenyl dichlorophosphate (Table 9, entry 4),[‌326‌] triphenylphosphine dichloride (Table 9, entry 5),[‌327‌] trifluoroacetic anhydride (Table 9, entries 6 and 7),[‌328‌‌331‌] acetic anhydride,[‌332‌] sulfur trioxide/pyridine,[‌333‌] or phosphorus pentoxide.[‌334‌] Treatment with base generates the ylide 115, which releases the ketone 116 by a hydrogen shift. Many of the older applications of this method have been reviewed.[‌5‌,‌335‌]

Meeeee 88 Meeeeeeee ee eee Meeeeeeeee ee Meeeeeee eeee Meeeeee eeee Meeeeeee Meeeeeeee ee eee Meeeeeee ee ee Meeeeeeeeeee

Me eeeeeeeee eeeeeeeee ee eee eeeeeeeee eeee eeeeeeeee eeeeeeee eeeeeeeee ee eee eeee eeee eeeeeeeeee eeeeee eeeee eeee eeeeeee ee eeeeeeeee eeeeeeee eee eee eeeeeeee ee eeee eeeeeee.[‌8‌] Meeee eeeeeeeee,[‌888‌] eeeeee, eee eeeee-eeeeeeeee eeeeeee eeeeee[‌888‌] eee eeeeee eeeee eeeee eeeeeeee eeeeeeeeee. Mee eeeeeeeee ee eee,eee-8,8-eeeee eeee eeeeeeeee eeeeeeee eeeeeeeee eeeeeeeee eeeeee eeeeee eee α-eee eeeee eeeeeee eeeeeeee ee MM eeeee.[‌888‌,‌888‌,‌888‌]

Meeee 8 Meeeeeeee ee Meeeeeee ee Meeeeee ee Meeeeeeee Meeeeeee Meeeeeeee (Meeee Meeeeee)[888,888,888-888,888,888]e

Meeee Meeeee Meeeeeeeee Meeee Meeeeeeeeee Meeee (%) Mee
8 eeeeeeeeeee-8,8-eeeeee (MMMe)8 (8.8 eeeee) MMMM (8.8 eeeee), MM8Me8, 88°M, 88eee; Me8M (eeeeee), 88°M ee ee, 8e 88 [‌888‌]
8 8-(8-eeeeeeeeee)­eeeeeeeeeeeee (MMMe)8 (8.8 eeeee) MMMM (8.8 eeeee), MM8Me8, 88°M, 88eee; M-eeeeeeeeeeeeeee, 88°M ee ee, 8e 88 [‌888‌]
8 8,8-eeeeeeee­eeeeeeeeeeeee MeMM8MMe8 (8.8 eeeee) MMMM (8.8 eeeee), MM8Me8, Me8M (8 eeeee), 88°M ee ee, 8e 88 [‌888‌]
8 eeeee-8-eee Me8MM(MMe) (8 eeeee) MMMM (8 eeeee), eeeee, MM8Me8, 88°M; Me8M (8 eeeee), 88°M ee ee, 88eee 88 [‌888‌]
8 eeeeeeee Me8MMe8 (8.8 eeeee) MMMM (8 eeeee), MM8Me8, 88°M, 8e; Me8M (8 eeeee), 88°M ee ee, 8e 88 [‌888‌]
8 8-eeeeeeeeeeee­eee-8-eeeeee MMMM (8 eeeee) MMMM (8 eeeee), eeeee, MM8Me8, 88°M, 88eee; Me8M (8.8 eeeee),88°M, 8.8e 88 [‌888‌]
8 8,8-eeeeee-8-eee MMMM (8.8 eeeee) MMMM (8 eeeee), eeeee, MM8Me8, 88°M, 88eee; Me8M, ee 88 [‌888‌]

e Mee Meeeee 88.

e Meeeeeeeee ee MMMM ee eeeeeeeee ee eee eeeeeeeeeee eeeeeeeee eeeee ee eee eeeeeeee ee eee eeeeeee eee eee eeee.

e Mee eeeeeeeee ee eeeeeeeeeee-8,8-eeee.

e Mee eeeeeeeee ee eee-eeeeeeeeeee-8,8-eeee.

Me eeeeeeeeee eeeee eee eeeeeeee eeeeeeeee ee 8,8,8-eeeeeeeee-8,8,8-eeeeeeee, eeeee eeeeeeeee eeeeeeeee eeeeeee ee eeee eeeeeeeee.[‌888‌] Mee eeeeeeeeeeee M-eeeeeeeee eeeeeeeee eeeeeeeeee eeeeee eeee eeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeeeee ee eeee eeeee ee eeeee ee eee eeeeeeeeeee ee eeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeeeee eee ee eeeeeeee ee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeee eeeeee.

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeeee ee 8-Meeeeeeeeeeeeeeeee eeee Meeeeeee Meeeeeeee eee 8,8,8-Meeeeeeee-8,8,8-eeeeeeee ee Meeeeeeeee Meeee[‌888‌]

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

Meeeee 88 Meeee Meeeeeeee eeee eee Meeeeeeeee Meeee ee Meeee Meeeeee[‌888‌]

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

Meeeee 88 Meeeeeeeeee ee Meeeeee ee Meeeeeeee eeee e Meeeeeeeeee Meeeeeeee (Meeeeeee Meeee Meeeeeeee)[‌888‌]

Me eeeeeeeeeee ee eeeeeeee eeeeeeeeee eee eeeeeeeee eeeeeeeeee ee eeeeeeeeeeee ee eee eee ee eee eeee(eeeeeeee eeeeee)-eeeee eeeeeeee eeeeeeeee 888. Meee eeeeeeeeee eeeeeee ee eeeee-eeeeeee, eeeeeeee, eee eee ee eeeeee eeeeeeee (Meeeee 88).[‌888‌] Meeeeeeee ee eeeeeeee ee eeeeeee eeeeee ee eeeeeeeee eeeeee ee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeee (88). Meee eeeeeeee eee eeee eeee eeeeeee[‌888‌] eeeee e eeeeeee eeeeeeeeeee-eeeee eeeeeeeee, eee eee eeeeee eee eeeeeeeeeeeee eeeee.

Meeeee 88 Meeeeeeeeee ee Meeeeee ee Meeeeeeee eeee Meee(eeeeeeee eeeeee) Mee(8-Meeeeeeeeeeeee)eeeeeeeee (Meeeeeee Meeee Meeeeeeee)[‌888‌]

Mee eeee ee eeeeeeee eeeeeee ee eee eee eeee eeeeee eee eee eeeeeeeeee eee ee eeeeeeee eeeeeeeee. Mee eeee eee eeeeeeeeee eeee eeeeeeeeee eeeeeeee ee eeee e eeeeee. Meee eeeeeeeeeeeee eee ee eeeeeeee ee eeeee eeeeeeeee eeeeee eeeeeeeee. M-(eeee-Meeee)eeeeeeeeeeeeeeeeeeee eeeeeeee (888) eee eeee eeeee ee ee ee eeeeeeeeeee eeeeeeeeee eee eee eeeeeeeee eeeeeeee eeeeeeeee.[‌888‌] Meeeeee eee eeeeeeee eeee eeeeeeeee eeeeeeee eeee 888 ee eeeeeeeee eeeee eeee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee eeee ee eee eeee eeeeeee ee eee eeeeeeeeeeeee eeeeeee ee eee eeeeeeeee Meeee eeeeeeeee. M eeeeeeeeeeeeee eeeeeee eee eeee eeee ee eeeeeeee ee eee eeeeeeeeee ee eeeeeeee-8-eeee (888) eeee eeeeeeee-8-eeeee (88) (Meeeee 88).[888]

Meeeee 88 Meeeeeeee ee Meeeeeee-8-eeee ee Meeeeeee-8-eeeee eeee M-(eeee-Meeee)eeeeeeeeeeeeeeeeeeee Meeeeeee[‌888‌]

Mee eeeeee eeeeeeeeeeee eee eee eeeeeeeee ee eeeeeeee eeee eeeeeeee eeeeeeeee ee eee eee­eeeeeeeeeeee eeee 888 (Meeeee 88) eeeee eee eeee ee eeeeeeee ee eeeeeeeeeeee ee eee eeeeeee eeee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeee­eeeee. Meee eeeeee ee eeeee ee MeeeeeeeMeeeeee eeeeeeeee.[‌888‌] Me eee eeee eeeeee eeee eee eeeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeeeeee.[‌8‌] Meeee eeeeeeeee eee eeeeeee eeeeeee eee eeee eeee eeeeeeeeeee, eee eeeeee eeeeeeeee eeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeee ee eee eeeeeeeeee ee eeeeeeeeeeeeeeee. Meeeeeeeeee eee eeee ee e eeeeeee eeeee eee eeeeee eeeeee eeeeeeeeee ee eeee eeeeeeeee, eee eee eeeeee ee eeeeeeee ee eeee eeeeeeeeee eeeeee.[‌8‌,‌888‌] M eeeeeee eeeeeee ee eee eeeeeeeeeee ee 8-eeee-eeeeee-8-eeeeee­eeeeeee (888) (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeee ee 8-eeee-Meeeee-8-eeeeeeeeeeeee eeee Meeeeeee Meeeeeeee ee eee MeeeeeeeMeeeeee Meeeeeeee[‌888‌]

Mee MeeeeeeeMeeeeee eeeeeeeee eee eeee ee eeee eee eee eeeeeeeeee ee 8,8-eeeee eeee 8,8-eeeeeeeee eeeeeee eee eeeeeeee ee eee eeeeeeeeee MM eeee.[‌888‌] Me eeeeeeeeeee eeeeeeeee ee eeee eeeeeeee ee eee eeeeeeeee ee eeeeeeee ee eeeee-8,8-eeeeeee (888) ee eeee eeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeee ee Meeeeeee eeee Meeee-8,8-eeeeeee ee MeeeeeeeMeeeee Meeeeeeee[‌888‌]

Meeeeeeeee eeeeeeeee eee eeee eeeeeeee ee e eeeeeeeeee eeeee ee eee eeeeeeeee ee eeeeeeee eeee eeeeeeee eeeeeeeee. M eeeeee ee eeeeeeeee eeeeeeeee eeeeee eeee eeee eeeeeeeeeeee eeeeeeee eeee eeee eeeeeee.[‌8‌] Mee eeeeeeee ee eeeeeee eeeeeeeee ee eeeeeeee eeee­eeeee ee eeeeeeee eeeeeeeeeee eee eeeeeeee eeeeeee eeee ee eeee, ee eeeee eee eee eeeeeeeeeee ee eee eeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee e Meeeeeeee Meeeeeeee Meeeeeee eeee Meeeeeee Meeeeeeee ee eee Meeeeeee ee Meeeeeeeeee Meeeeeeee ee eee Meeeeeeeee Meeee[‌888‌]

Meeeeee eeeeeeee eeeeeeeeeee eeeee, eeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee ee 8-eeeeee-8,8-eeeeeeeeeeeeeeeeeee eeeeeeee (888), eeeee eeeeeee eee eeeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeee ee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee (Meeeee 88).[‌888‌] Meeee eeeee eeeeeeeeee eeeeeee eeeeeeee eeeeeee eeeeeeeeeeee.

Meeeee 88 Meeeeeeeee ee Meeeeeeee Meeeeeee eeee Meeeeee eeee Meeeeeee Meeeeeeee eee 8-Meeeee-8,8-eeeeeeeeeeeeeeeeeee Meeeeeee ee eee Meeeeeeeee Meeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-(8-Meeeeeeeee)eeeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

Meeee e eeeeee ee eee M8, ee eeee-eeeee 888-eM eeeee-eeeeeeee eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee eee MM8Me8 (88eM). Meeeee eeeeeeee (8.8eM, 8eeee) eee eeeee eee eee eeee eeeeee ee 88°M. MMMM (8.8eM, 88eeee) eee eeeee eeeeeeee eeee 88eee. Meeee 88eee, e 8M eeee ee 8-(8-eeeeeeeeee)eeeeeeeeeeee (8.88e, 8eeee) ee eee MM8Me8 eee eeeee eeeeeeee eeee 88eee. M-Meeeeeeeeeeeeee (8.8eM, 88eeee) eee eeeee eeeeeeee eee eee eeeeeee eee eeeeeee eee ee eeeeeeeeee 88eee. Mee eeeeeee eeee eee eeeeeee eee eee eeeeeee eee eeeeeee ee eeeee 8°M. Mee eeee eee eeeeee eeee eeeeeee eee eeeeeeeeee 8M MMe (8eM), eee eee eeeeeee eeeee eee eeeeeeeee eeee eee ee MMe (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee ee 8°M, eee eeeeeeee eeee eeeee MeMM (8.8e). Meeeeeeeee eeee Me8M (8×88eM) ee eee eeeee eeeeeee eeeee, eeeeeeee ee eeeeee (MeMM8) eee eeeeeeeeeee ee eee eeeeeeee eeeeeee eeeeeeee, eeee e eeeeeee ee 8-(8-eeeeeeeeee)eeeeeeeeeeeee eee M-eeeeeeeeeeeeeee. Mee M-eeeeeeeeeeeeeee eee eeeeeeeeee (88°M/8.8Meee), eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeee eeeeeeeeeeee ee eeeee e ­eeeeeeeee eee; eeeee: 8.88e (88%); ee 88°M/8.8Meee.

Meeeeee 888 ee Meeeeeeee eeee Meeeeeee MeeeeeeeeMeeeeeeeeeeeeeeeee Meeeeeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

MMMM (8eeee) eee eeeee ee e eeee ee eeeeeeeeeeeeeeeeee eeeeeeee (8.8eeee) ee MM8Me8 (8eM) ee 88°M. Mee eeeee ee eee eeee eeeeee eeeeee eeee eee eeeeeeeee eee eeee eee eeeee eeeee eeee eee eeeeeeeeee. Meeee 8e, e eeee ee eee eeeeeeeeeee eeeeeee (8eeee) ee MM8Me8 (8eM) eee eeeee eee eee eeeeeee eee eeeeeee ee eee eeee eeeeeeeeeee eee 88eee, eeee Me8M (8eeee) eee eeeee. Mee eeeeeee eee eeeeeee ee eeee ee ee (8e). Meee ee eee MM8Me8 eee eeeeeee ee eeeee, eee e eeeeeee ee Me8M/eeeeee (8:8) eee eeeee ee eeeee ee eeeeeeeeeee eeeeeeeeeeeeeeeeee eeeee, eeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeeee eee eeee eeeeeee; eeeee: 8888%.

Meeeeee 888 ee Meeeeeeee ee Meeeeee Meeee eeee Meeeeeeeeeeeeeee Meeeeeeee Meeeeeeee Meeeeeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeeeeeeee eeeeeee eeee ee MMMM (888μM, 8.88eeee) ee MM8Me8 (88eM) eeeeeeeeee eeeee ee eeeee eeeeeeeeee ee 88°M (eee eee ee eee M8/MMMe8 eeee) eee eeeeeee eeeeeeee eeee MMMM (888 μM, 8.88eeee). Mee eeeeeeeee eeeee eeeeeeeee eeee eee eeeeeee ee 88°M eee 88eee, eee eeee eee eeeeeeeeeee eeee (8.88eeee) eeeeeeeee ee e eeeeeee eeeeee ee MM8Me8 ee MM8Me8/MMMM eee eeeee ee e eeeeeeee eeeeeee. Mee eeeee eeeeeeeee eeee eee eeeeeee ee 88°M eee 8.8e. Meeee eee eeeeeeee eeeeeeee ee Me8M (8.88eM, 8.88eeee), eee eeeee eeeeee eeeeeee eee eeeeeee eee e eeeeeee 8.8e ee 88°M, eeeeee ee ee. 8°M, eeeeee eeee ee 8M MMe (88eM), eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (88eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee, eeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeeeee; eeeee: 8888%.

Meeeeee (88) ee Meeeeeee Meeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee eeeeeee eeee ee eeeee MM8Me8 (8eM) eeeee eeeee ee 88°M eee eeeee eeeeee eeeeeeee (8.88eM, 8.8eeee). 8-(Meeeeeeeeeeeee)eeeeeeeeeee eeeeeeeee (8.8e, 8.8eeee) eee eeee eeeee eeeeeeee eee eee eeeeeee eee eeeeeee eee ee eeeeeeeeee 88eee. Meeeeeeeee (8.888e, 8.8eeee) eeeeeeeee ee MM8Me 8 (8eM) eee eeee eeeee ee eeee eeee eeeeeeee, eeeee ee eeeeeeeeee 8.8 ee 8e, ee eMe8MMe (8.88eM, 8.8eeee). Mee eeeeeee eee eeee eeeeeee ee eeee ee ee eee eeeeeee eee e eeeeee ee 88eee eeeeee ee eee eeeeeeee eeee M8M, eeeeee eeee MM8Me (8eM), eeeeeeeee eeee MM8Me8 (88eM), eee eeeeeeeee eeeeeeeeeeee eeeee eeeeeeeee eeeeee ee e eeee eeeee eeee. Mee eeeeeee eee eeee eeeeeeeee ee eeeeeee (8eM) eee eeeeeeeee eeeeeeeeeeee eeee eeeeeeeeeeeeee eeeeee (88eM) ee e eeeeee eeeeeeeeee eeeeeeeee eee 8e. Meeee eeeeeeeeeee, eeeeeeeeeeeee ee eee eeeeeee eeeee eee eeeeeeeeeeeeee (eeeeee eee) eeee eee eeee eeeeeee; eeeee: 8.888e (88%).

Mee eeeeeeee eeeee, eeeeeeeeee e eeeeeee ee 8-(eeeeeeeeeeeeee)eeeeeeeeeee eeeeeee eee 8-(eeeeeeeeeeeeee)eeeeeeeeeee eeeeeeeee, eee eeee eeeeeee eeee MeMM (8eM) eee 88% M8M8 (8.88eM, 8eeee) eee 8e, eeeee eeeee ee eee eeeeeee eeee M8M (8eM) eee eeeeeeeee eeee MM8Me8 (88eM) ee e eeeee-eeeee eeeeee. Meeeeeeeeeeee ee eee MM8Me8 eeeee eeee eee eeeeeeeee 8-(eeeeeeeeeeeeee)eeeeeeeeeee eeeeeeeee; eeeee: 8.8e (88%).

Meeeeee (88) eeee e Meeeeeee Meeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeeeee-eeeeeeeee eeeeeeee eeeeeeeee 888 (e=88; 8.88e, 8.88eeee) ee MM8Me8 (88eM) eee eeeeee ee eeeeeee 88 eee 88°M, eee eeeeee eeeeeeee (8.888eM, 8.888eeee) eee eeeee eeeeeeee, eeeeeeee eeeee 88eee ee e eeee ee eeeeeeeeee (8.88eeee) ee MM8Me8 (8eM). Mee eeeeeee eee eeeeeee eee 88eee, eeee Me8M (8.88eM, 8.8eeee) eee eeeee, eee eee eeee eee eeee ee 88°M eee 8.8e eeeeee eeeeeee ee ee. Meeeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeee ee eeeeee. 88eM, eeeeeeee ee eeeeeeee ee Me8M (888eM) ee eeeeeeeeeee eee eeeeeee. Mee eeeeeeeeeeeee eee eeeeeeeeeee ee eeeeeee ee 88°M eee 88eee. Meeee eeeeeeeeee, eee eeeeeeee eee eeeeeeeeeeee ee eeeee ee eeee eee eeeeeeee eeeeeee, eeeee eeeeeeeee eeeeeeeee e eeeee ee eeeeeee eeeeeeeeeeeee (8%); eeeee: 88%; eee eeeeeeeee eeeeeeeeee eeeee eeeeee ee eeeeeee ee eeeeeee ee eeeeeeee eeeeeeeeee eeeeeee e eee ee eeeeee eee.

8-eeee-Meeeee-8-eeeeeeeeeeeee (888):[‌888‌]

8-eeee-Meeeee-8-eeeeeeeeeeee-8-ee (88.8e, 8.888eee), MMM (88.8e, 8.888eee), eeeeeeee (8eM), eee MMMM (88eM) eeee eeeeeeeee ee eee Me8M (888eM). Meee eeeeeee eee eeeeee ee 8°M, MMM (8eM) eee eeeee, eee eee eeeeeeee eee eeeeeee eeee eee eee eeee. Meeee eeeee 88eee, eee eeeeeeee eeeeeeeeeeee eeeeee ee e eeeeee eeeeee eeeee eeee eeeeeeee. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeee ee ee eee eeee, eee eeeeee eeee (88e) ee MeMM (88eM) eee eeeee ee eeeeeee eeeeee MMM. Mee eeeeeeeeeeee eeee eee eeeeeeeee eee eeeeee eeee Me8M (8×888eM). Mee eeeeeeeee eeee eeeeee eeee M8M (888eM), 8% MeMMM8 (8×888eM), eee eee. MeMe (888eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee ee eeeee. Mee eeeeeeee eee eee eeeeeeeee ee eeee eee eeeee eeeeeeee ee e eeeeeeeee eeeeee; eeeee: 88.8e (88%); ee 88°M/8Meee.

Meeeee 8,8-M-Meeeeeeeeee-8-M-eeeee-α-e-eeee-eeeeeeeeeeeee-8-eeeee (888):[‌888‌]

M eeeeeee ee eeeeee 8,8-M-eeeeeeeeeee-8-M-eeeee-α-e-eeeeeeeeeeeeeee (8.8e, 88.8eeee), MMMM (8e, 88eeee), M8M8 (8e, 88eeee), eee MMM (888eM) eee eeeeee eee 8e ee 8888°M eeee eeeeeeee. Mee eeeeeee eee eeeeee eeee eee eeeee, eee eee eeeeeeee eee eeee ee e eeeeeeeeeeee eeeeeeeee. Mee eeeeeeee eeee eeeeee eeee eeeeeeeee ee eeeeeeeeee eee eeeeee eeeeeeeeee eeee M8M. Meeeeeeeeeeeeee (MeMM) eeee eee eeee eeeee eeeeeeee ee eeeeeeeee eeeeeeee; eeeee: 8.8e (88%); ee 888888°M; [α]M +88.8 (e 8.8, MMMe8).