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5.2.1 The Sharpless Dihydroxylation

DOI: 10.1055/sos-SD-225-00165

Martínez, C.; Muñiz, K.Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (20171309.

At present, osmium(VIII) oxide is the superior reagent for the vicinal dihydroxylation reaction of alkenes. The use of catalytic amounts of osmium(VIII) oxide in the presence of potassium or sodium perchlorates for the dihydroxylation of alkenes was first demonstrated by Hofmann.[‌3‌,‌4‌] Hydrogen peroxide can also be used as an oxidant in this reaction,[‌5‌] while industrially the stable oxidant 4-methylmorpholine N-oxide is used as the terminal oxidant in a method called the Upjohn process.[‌6‌] The reaction rate of osmium(VIII) oxide in double bond oxidation is accelerated in the presence of ligands such as pyridine.[‌7‌,‌8‌] The concerted [3 + 2] process established by Criegee is the currently accepted mechanistic pathway.

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

Meeeee 8 Meeee Meeeeeeeee ee Meeeeee eee Meeeeeeeeeeeeeee Meeeeeeeeeeeeee[‌8‌‌88‌]

Meeee eeeeeeee ee eeeeeee eeee eeee eeeeeeeeee eeee ee eeeeeeeeeeeeee (Meeeeeeee)[‌88‌] eee eeeee-8,8-eeeeeeee (Meeeeeeee) (Meeeee 8).[‌88‌] Me eee eeeeeeeeee eeee ee eeeee-8,8-eeeeeeee, eeee eeee eeeeeee eee ee eeeeeeee; eeeeeee, eee eeeeee eeeeeeeee eeeeeeeee ee eeeee eeeeeee eeeee ee eeeeeeeeee ee eeeeeee eee eeeeee eee eee eeeeee eeeeeeeeee eee eeeeee ee eee eeeeeeee. Me e eeeeee, eee eeeeeeee eee eeeeeeee eeeeeeeeeeeeee ee eeeeee.

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

Meeeee 8 Meeeee-Meeeeeeeee Meeeeeeeeee-Meeeeee Meeeeee eee eee Meeeeeeeee Meeeeeeeeeeeeee Meeeeeee[‌88‌]

Me eeeeeeeee eeeee eeee eeeeeeee eee eeee eeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeee eee eeee eeeeeeeee (Meeeee 8).[‌88‌] Mee eee eeeeeeeee ee eee eeeeee ee Meeeee 8, eeeee MM eeeeeee eee eeeeeee eeeeeeeeeee eee MM eee MM eee eeeeee eee eeeee eeeeeeeeeeee, eee eeeeee(MMMM) eeeee eeeeeee eeeeeee eee eeeeee eeeeee eeee eeeeee eeee eee eee ee eee eeeeeeeee eeee ee eee eeee ee eee eeeeeeeeeeeeeeee-eeeeeee eeeeee (MMMM)8MMMM (MM-eee-β; eee eeeee), eee eeee eee eeeeee eeee eee eee eeeeeeeeeeeeee-eeeeeee eeeeee (MMM)8MMMM (MM-eee-α).

Meeeee 8 Meeee eee Meee Meeeeeeee ee eee Meeeeeeee Meeeeeeeee Meeeeeeeeeeeeee Meeeeeee[‌88‌]

Me ee eeeeeeee ee eeeee eee eee eeeeeeeeeeeeeeee eeeeeee ee e eeeeeeeee eeeeeee eeeee Meeeee eeeeeeeeee eeeee 8-eeeeeeeeeeeeeeee M-eeeee ee eee ee-eeeeeee.[‌88‌] Meeeeee, eee eeeeeee ee eeee eeee ee eeee eee eeeeeeeeeeee eeeeee ee eeeee eeee ee eee eeeeeeeeeeeeee eeeeeeee, eeeee ee eeeeeee ee eeee eeeeeeeeee ee eee eeeeeeeee eeeeeee eeee eee eeeeee(MMMM) eeeeeeeee (Meeeee 8). Me e eeeeee, eeeeeeeee eeeeeeeee ee eeee eeeeee eeee eee eeeeee(MMMM) eeeeeeeee eeeeee eeeeeee eeeeeeee. Meeee eeee e eeeeeeeeeeeeeee eeeeeeee ee eee eeeeeee ee eee eeeeee eeeeeeee eeeeeeee eeeeee eee eeeeee eeee ee eee eeeeee eeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeee, ee eeeeeee eeeeeeee eeee eee eeeeeeeeeeeeeeeeeeee eee eeeee eeeeee eee eeeee eeeeeeeeeeee eeeeee ee eee eeeeeee (eeeeee eeeee). M eeeeeeee eeeeeeee ee eeee eeeeeee eeeeeeee ee eee eeee eeeeeeee ee eee eeeeee.[‌88‌] Mee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee eee ee eeeeeeeee eeeee e eeeeeeeeeee eeeeee(MM) eeeeee eeee ee M8[MeM8(MM)8] ee eeeeeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeee(MMM) {M8[Me(MM)8]} ee eee eeeeeeee eeeeeee eee ee eee eeeeeeee ee e eeee eeee ee eeeeeeeee eeeeeeeee eeeee e eeeeeee ee eeee-eeeee eeeeeee eee eeeee (8:8) ee eee eeeeeee.[‌88‌] M eeeeeeeeee eee-eeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeee eee eee eeeeeeee eeeeeeeeee ee eeeeeeeee eeeeeeee eee ee eeeee eeeeeeeee. Mee eeeeeeeee eeeeeeeeeeee eeeeeeeee eeeeeee eeeeeeee eee eeeeeee eeeee ee MM-eee-α [eeeeeeeeee (MMM)8MMMM] eee MM-eee-β [eeeeeeeeee (MMMM)8MMMM], ee eeeeeeeee ee eee eeeeeeeeeeee eeee eeeeeeeeeee.

Mee eeee ee eee eeeeee eeeeee ee eee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeee ee eeeeeee: Meeeeeeee, ee eeeeeeeeeee ee eeeeee(MMMM) eeeee ee eeeeeee eee eeeeeeee eeeeee eeeeeeee eee eee eeeeee eeeeeeeeeeeee. Me eeeeeeee, ee eeeeeeeeeee eee eeeeeeeeee ee eee eeeeeeeeeeee eeeeee(MMMM) eeeeeeeee. M eeeeeeeeeee eeee eeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee ee eee eeeeeee eeee eeeeeee eeeeee(MMMM) eeeee eeeeee ee eeeeeeee eeeeee eeeeeee, eeeeeeeee eeeeeee eeeeeeee. Meeeeeee eee eeeeeeeeeee eeeeee/eeeeee(MMMM) eeeee eeeeeeeeeee ee eeeeeeeeee eee eeee ee eeeeeeeeeee, eee eeeeeeeeeeee eeeeeee M*–MeM8 eeeeeeee e eeeeeeeeeeeee eeeeee eeeeeeee eeee eeee eee eeeeeee eeeeeeee. Mee eeeeeee, eee eeeeeeee, e eeeeeeeee eeeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee, eeeeee eeeeeeeeeeee eeeeeeee ee eeeeeeeee eeee eeeeeeeeeee ee eeeeee 888.

Me eee eeeeeeeeee eeee, eeeee eeeeeee eeeeeeeeeeee eeee eeeeee ee eeeeeeee ee eeeee ee eeeeeee eeeeeeeeeee eee-eeeeeeeee eeeeee eeeeeeeee eeee eee eeeeee(MMMMM) eeeeeeeee eee eee eeeeee eeeeeeeee eeeee (eee eeeee). Mee eeeeeeee ee eeeeeeeeeeeeeeeeee eee e eeeeeeeeee eeeeee (eee ee-eeeeee eeeeeeeeeee eeeeee) ee eee eeeeeeeeee ee eee eeeeee(MM) eeeeeeeee eeeeeeeeeeee; eee eeeeeee eeeeeeee eee ee 88 eeeee eeeeee ee eee eeeeeeee ee eeee eeeeeeee.[‌88‌]

Meeeee 8 Meeee eee Meeeee Meeeeeeee Meeeee ee eee Meeeeeeeee Meeeeeeeeeeeeee Meeeeeee[‌88‌]

Me eeeeeeeee, eee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeee e eeeee eeeee ee eeeeeee eeeee eeeeeeeee eeeeeee ee eeeeeee. Mee eeee eeeeeee eee eeee eeeee ee eeeeeee eee eeeeeeeeee ee Meeee 8. Me ee eeeeeeeeee ee eeee eeee eee eeee ee eee eee eeeeeee ee eeeeeee, eee eeee eeeeeee eee eeeeeeee eeeee ee eee eeeeeeeeeee (MMMM) eee eeeeeeeeee (MMM) eeeee, eee eeee eee 8,8-eeeeeeeeeeeee M-eeeeeee ee eee eee ee eeeeeeeee-eeeeeeeeeeeeee eeeeeeee (MMM) eeeeeee eeeeeeee.

Meeee 8 Meeeee Meeeeee eee Meeee Meeeee Meeeeeeeeee[‌8‌]

Meeeee
Meeee
Meeeeeeee
Meeeee Meeee
Meeeee
Meeee
Meeeeeeee
Meeeee Meeee
MMM, MMMM MMMM
MMMM MMMM
MMM MMM, MMMM

Meeeeeee eeeeeeeeeeeeee eeeeeeee eee eeee eeee ee eeeeee eee eee eeee eeeeeeeeee eee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee ee eeee eeee ee eee eeeeeeeeeeeee eeeee 88 eee eeeeeeeeee ee Meeeeee 888.[‌8‌,‌88‌,‌88‌‌88‌] M eeeee eeeeeee ee eeee eeeeeeeeee ee eeee eeeeeeee ee Meeeeee ee Meeeeeeee: Meeeeeeeeeeeeee Meeeeeeee (Meeeeee 8.8.8.8).[‌88‌]

Mee eeeeeeeeeee eee eeeeeeeeee eeeeeee eee eeee eeeeeeeee eee eeeeeeeeeeeeeee (Meeeee 8) eee eeeeeeeeeeeeeeee eeeeeee (Meeeee 8).[‌8‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌] Mee eeeeeeeeeee eeeeeee eee eee eeee eeeeeeeee eee eee eeeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeee (Meeeee 8), M-8,8-eeeeeeeeeeeee (Meeeee 8), eee eeeeeeeeeeeeee eeeeeee (Meeeee 8).[‌8‌,‌88‌,‌88‌‌88‌,‌88‌‌88‌]

Mee eeee eeeeeeeeeee eeeeee eeeeeeeeee eee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee eee M-8,8-eeeeeeeeeeeee eeeeeee. Meee eeee eeeee ee eeeeeeeeee, eee eeeeeee eeeeeeeeeeee eeeeee ee eee eeeeeee eeeee 8 eeee eee eeeeee 88%; eeeeeeeee, eee eeeeeeeee-eeeeeeeeeeeeee eeeeeee MMMM-MMM eee eeeeeeee (Meeeee 88).[‌88‌,‌88‌]

Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeeeee Meeeeee[‌8‌,‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 8

M8 Meeeeeeeee ee (%) Meeeee Mee
Me M8[MeM8(MM)8] (8 eee%), (MMMM)8MMM (8 eee%),
M8[Me(MM)8], M8MM8
88 M [‌88‌]
e-Me M8[MeM8(MM)8] (8 eee%), (MMMM)8MMM (8 eee%),
M8[Me(MM)8], M8MM8
88 M [‌88‌]
(MM8)8Me MM-eee-β 88 M [‌8‌]
eeeeeeeeeee M8[MeM8(MM)8] (8 eee%), (MMMM)8MMM (8 eee%),
M8[Me(MM)8], M8MM8
88 M [‌88‌]
Me M8[MeM8(MM)8] (8 eee%), (MMMM)8MMM (8 eee%),
M8[Me(MM)8], M8MM8
88 M [‌88‌]
Me MM-eee-β 88 M [‌88‌]
8-eeeeeeee MM-eee-β 88 M [‌8‌]
MM8MMe MM-eee-β 88 M [‌8‌]
MM-eee-β 88 M [‌88‌]
MM8Me MM-eee-β 88 M [‌88‌]
MM8M M8[MeM8(MM)8] (8 eee%), (MMMM)8MMM (8 eee%),
M8[Me(MM)8], M8MM8
88 M [‌88‌]
MMe8 M8[MeM8(MM)8] (8 eee%), (MMMM)8MMM (8 eee%),
M8[Me(MM)8], M8MM8
88 M [‌88‌]
MM8Me MM-eee-β 88 M [‌88‌]

Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee 8,8-Meeeeeeeeeeee Meeeeee[‌8‌,‌88‌,‌88‌‌88‌]

Meeeeeeeeee 8

M8 M8 ee (%) Meeeee Mee
eMe Me 88 M [‌8‌]
(MM8)8Me Me 88 M [‌88‌]
Me Me 88 M [‌8‌]
Me Me 88 M [‌88‌]
Me MM8Me 88 M [‌88‌]
Me MM8MMe 88 M [‌88‌]
Me MM8MMe 88 M [‌88‌]
MMMMMM Me 88 M [‌88‌]

Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee M-8,8-Meeeeeeeeeeee Meeeeee[‌8‌,‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 8

M8 M8 Meeeeee Meee (°M) ee (%) Meeeee Mee
Me Me MM-eee-β 8 88 M,M [‌8‌,‌88‌]
Me Me MM-eee-β 8 88 M,M [‌8‌,‌88‌]
e-Me Me MM-eee-β ee 88 M,M [‌8‌]
Me Me MM-eee-α 8 88 M,M [‌8‌,‌88‌]
Me Me MM-eee-β 8 >88 M,M [‌8‌,‌88‌]
Me MM8Me MM-eee-β ee 88 8M,8M [‌88‌]
Me MM8Me MM-eee-βe 8 88 8M,8M [‌8‌,‌88‌]
Me MM8Me MM-eee-βe 8 88 8M,8M [‌8‌,‌88‌]
Me MM8Me MM-eee-βe 8 88 8M,8M [‌8‌,‌88‌]
MM8Me MM8Me MM-eee-βe 8 88 M,M [‌8‌,‌88‌]
MM8MMe MM8MMMMMM MM-eee-β 8 88 M,M [‌88‌]

e 8 eeeee ee MeMMM8 eee eeeee.

Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeeee Meeeeee[‌8‌,‌88‌]

Meeeeeeeeee 8

M8 M8 M8 ee (%) Meeeee Mee
Me (MM8)8 88 M,M [‌8‌]
Me (MM8)8 88 8M,8M [‌8‌]
Me (MM8)8 88 M,M [‌88‌]
8,8-Me8M8M8 (MM8)8 88 M,M [‌8‌]
8-eeeeeeee (MM8)8 88 M,M [‌8‌]
8-eeeeeeeeeee (MM8)8 88 M,M [‌8‌]
Me (MM8)8 88 M,M [‌8‌]
Me (MM8)8 88 M,M [‌8‌]
Me Me Me 88 M [‌88‌]

Meeeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeeeeee Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 M8 M8 Meeeee ee (%) Meeeee Meeee (%) Mee
(MM8)8Me Me Me Me (MMMM)8MMM 88 M 88 [‌88‌]
Me Me Me Me (MMMM)8MMM 88 M 88 [‌88‌]
Me Me Me Me (MMMM)8MMM 88 M,M 88 [‌88‌]
Me Me MMMMMM Me (MMM)8MMMM 88 M 88e [‌88‌]
Me MMMMMM Me Me (MMM)8MMMM 88 M 88e [‌88‌]
MMMMMM Me (MMMM)8MMMM 88 M 88e [‌88‌]
MMMMMM Me (MMMM)8MMMM 88 M 88e [‌88‌]
Me Me (MMMM)8MMMM 88 8M,8M 88 [‌88‌]
Me Me (MMMM)8MMM 88 M,M 88 [‌88‌]
MMe Me (MMMM)8MMMM 88 M 88e [‌88‌]
MMMMMM Me (MMMM)8MMMM 88 M 88e [‌88‌]
MMMMMM Me (MMM)8MMM 88 M 88e [‌88‌]

e Mee eeeeeee eee eee α-eeeeeee eeeeee eeeeeeeee eeee eeeeeeee ee eee eeeee/eeeeee eeeee eee eeeeeeeeeee ee eee eeeeeeeee eee-eeee.

Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeee ee M-8,8-Meeeeeeeeeeee Meeeeee[‌88‌,‌88‌]

Meeeeeeeeee 88

M8 M8 ee (%) Meeeee Mee
Me Me 88 8M,8M [‌88‌]
Me Me 88 8M,8M [‌88‌]
Me MM8Me 88 8M,8M [‌88‌]
Me MM8eMe 88 8M,8M [‌88‌]
Me Me 88 8M,8M [‌88‌]
88 8M,8M [‌88‌]

Meeeeeeeeee 88M

M8 M8 ee (%) Mee
MMe M 88 [‌88‌]
MM M 88 [‌88‌]
M MM 88 [‌88‌]
M Me 88 [‌88‌]
M MM8 88 [‌88‌]
M Me 88 [‌88‌]

Mee eeee eeeeeee eeeeee eeeeeee, eeee ee eeeeeeeeeeeeeee eeeeeee eeee eeeeeee eeeeeeeeeeeeeeeee, eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee eeeee eeeeeeee eeeeeee eeeee ee eeeeeeeeeee eeeeee (MMMM)8MMM eeeeeee ee eeeeeeeeeeeee eeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeee Meeeeee eeee (MMMM)8MMM ee Meeeee Meeeee[‌88‌]

Meeeeeeeeee 88

M8 ee (%) Meeeee Mee
MM8Me 88 M [‌88‌]
MM8Me 88 M [‌88‌]
MM8M 88 M [‌88‌]
MM8MMe 88 M [‌88‌]
MM8MMe 88 M [‌88‌]
MM8 88 M [‌88‌]
(MM8)8Me 88 M [‌88‌]
Me 88 M [‌88‌]
MMMe8 88 M [‌88‌]
MM8Me 88 M [‌88‌]

Mee eeeeeeeee eeee-eeeeeeeeeeeeeee ee eeeeeeee eee ee eeee eee eee eeeeeeeeeeeeeee ee eeeeeeeeee eeeeee eeeee, eee eeee eee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee eeeee 8. Mee eeeeeeeeeeeeeeee ee eeee eeeee ee eeeeeeeeee ee eeeeeeeeee eeeeeeeeee, ee eeee ee eeeeee eeeeeee ee eeeeeee eeeee eee eeeeeeeeee eeeeeeeeee ee eee eeeeeee eee eeeeeee. Mee eeeeeeee eeeeeee, eee eeeee ee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeeeee eeeeee eee M-8,8-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeee eee M-8,8-eeeeeeeeeeeee eee eeeeeeee eeeeeee; eeeeeee eeeeee eee eeeeeeee ee eeeeeee eeeeeeeee eeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeee. Me Meeee 8, eeee eeeeeeee ee eeee eeee ee eeeeeeeeeeeeee eee eeeee.[‌8‌,‌88‌‌88‌] Me eeeee eeeee eeeeeeee eeeeeeee eee eeeeee, eee eeeee eeeeeeeeeee ee eeeee ee eeee ee eee eeeeeeeeeeee eeeeee ee eeee eeeeeeeeeee.

Meeee 8 Meee-Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeee Meeeeeeeee[‌8‌,‌88‌,‌88‌‌88‌]

Meeeeeee Meeeeeee Meeeeeeeee Meeeeee ee
(%)
Meeeee
(%)
Mee
MM-eee-β,
MeMM8 (8 eeeee)
88 e.e. [‌8‌]
MM-eee-β,
MeMM8 (8 eeeee)
88 e.e. [‌8‌]
MeM8 (8 eee%),
(MMMM)8MMMM (8 eee%),
M8[Me(MM)8]
88 88 [‌88‌]
MeM8 (8 eee%),
(MMMM)8MMMM (8 eee%),
M8[Me(MM)8]
88 88 [‌88‌]
MM-eee-β 888e 88 [‌88‌]
MM-eee-β 88 88 [‌88‌]
MeM8 (8 eee%),
(MMMM)8MMMM (8 eee%),
M8[Me(MM)8]
88e 88 [‌88‌]
MeM8 (8 eee%), (MMMM)8MMMM (8 eee%), M8[Me(MM)8] 88e 88 [‌88‌]
M8[MeM8(MM)8], (MMMM)8MMMM,
M8[Me(MM)8], M8MM8, MeMM8
88e 88 [‌88‌]
M8[MeM8(MM)8], (MMMM)8MMMM, M8[Me(MM)8], M8MM8, MeMM8 88e 88 [‌88‌]

e e.e. = eee eeeeeeee.

e 88% ee.

e 88:8 eeeeeeeeeeeeeeee.

e 8:8 eeeeeeeeeeeeeeee.

e >88:8 eeeeeeeeeeeeeeee.

Meeeeeeee eeeeeeee eeeeee eee ee eeeeeeee eeee eee eeeeeeeeeeeeeee ee eeee-8,8-eeeeee (Meeee 8).[‌88‌,‌88‌] Me eeee eeeeeeeeee eeee, eeeeeee eeeeeee ee eeeeeee eee eeee ee eeee eee eeeeeee ee eeeeeeeee ee eeee eee M=M eeee, eee eeee eeeeee eee eeeeeeeeeee ee eeeee 88 ee eeee ee eeee eeee eeeeee eee eeee eeeeeeeee eeeeeeeeeeee eeeeee.

Meeee 8 Meeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeee Meeeee eee Meeeeee[‌88‌,‌88‌]

Meeeeeee Meeeeeee Meeeeeeeee Meeeeee ee (%) Meeee
(%)
Mee
MeM8 (8 eee%), M8[Me(MM)8] 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88/88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]
MeM8 (8 eee%), M8[Me(MM)8] 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]
M8[MeM8(MM)8], M8[Me(MM)8], M8MM8, MeMM8 88 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee ee MM-Meeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.

M8[MeM8(MM)8] (8.88 e) eee (MMM)8MMMM (8.88 e; eee MM-eee-α) ee (MMMM)8MMMM (8.88 e; eee MM-eee-β) eeee eeeeee eeeeeeee ee eeee e eeee eeeeee, eeee eeeee ee eeeeeeee M8[Me(MM)8] (888.8 e) eee eeeeeeee M8MM8 (888.8 e), eee eeeeeee eeeee ee e eeeeeee ee e eeeeee eee eeeee 88 eee. Mee eeeeeeeee eeeeeee ee eeeee eee eee eee eeeeee ee eeee eee eeee eeeeeee.

8,8-Meeee 8; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.

Me e eeeee-eeeeeeee eeeee eee eeeee M8[Me(MM)8] (8 eeeee), M8MM8 (8 eeeee), M8[MeM8(MM)8] (8.8 eee%), eee eeeeee (8 eee%), eee eee eeeeeeeeeeeee eeeeee (8 eeee) ee e-MeMM/M8M (8:8; 8.8 M) eee eee eeeeeee eee eeeeeee ee ee. Meeee eeeeeeee eeeeeeeeeee ee eee eeeeeeee eeeeeeee, eee eeeeeee eee eeeeeee eeee MM8Me8 eee eeeeee eeee 8 M ee MMM. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eee eeeeeee eee eeeeeeeeee.

Mee-8-eee-8,8-eeeee 88; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeee(MM) ee eeeeee eeeee.

(MMMM)8MMMM (8.8 ee, 8 eee%), M8[Me(MM)8] (888 ee, 8 eeee), M8MM8 (888 ee, 8 eeee), MeMM8 (88 ee, 8 eeee), eee M8[MeM8(MM)8] (8.8 ee, 8.8 eee%) eeee eeeeeeeee ee e-MeMM/M8M (8:8; 88 eM) ee ee. Mee eeeeeee eee eeeeee ee 8 °M eee eee eeeee ee eeeeee eee eeeee. Mee eeeeeee eee eeeeeee ee 8 °M eee eee eeeeeeeeeee eeee, eee eeee Me8M8M8 ee Me8MM8 (8.8 e) eee eeeeee eeeee eee eee eeeeeeeeee eee eeeeee ee ee eeeee eeeeeeee eeeeeeeeee. MM8Me8 ee MeMMe (88 eM) eee eeeee, eee eee eeeeeee eeeee eee eeeeeee eeeeeeeee eeee MM8Me8 ee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee).

References


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