0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Julia–Kocienski and S. Julia Alkenation

DOI: 10.1055/sos-SD-047-00073

Markó, I. E.; Pospíšil, J.Science of Synthesis, (201047143.

In 1991, Sylvestre Julia (the brother of Marc Julia) reported a direct synthesis of alkenes starting from carbonyl compounds and α-metalated benzothiazol-2-yl sulfones (BT-sulfones; use of Bt to denote benzothiazol-2-yl should be avoided because this abbreviation is already extensively used in the literature for the benzotriazol-1-yl group) (Scheme 28).[‌153‌] Compared with the classical JuliaLythgoe alkenation method, the phenylsulfonyl group is replaced by a hetaryl sulfone moiety. This change profoundly modifies the reaction profile of the alkenation reaction, since the presence of an electrophilic imine-like function within the heterocyclic framework opens a new mechanistic pathway. The addition of α-metalated benzothiazol-2-yl sulfone 75 to an aldehyde proceeds smoothly (Scheme 28). However, the resulting β-oxy sulfone 76 is unstable and easily undergoes a Smiles rearrangement.[‌154‌] This rearrangement proceeds via the spiroannulated intermediate[‌155‌] 77 and results in the transfer of the heterocycle from sulfur to oxygen, yielding the sulfinate salt 78. Spontaneous elimination of sulfur dioxide and metalated benzothiazolone 79 from the intermediate 78 provides the alkene 80.

Meeeee 88 Meeeee Meeeeeeeee Meeee Meeeeeeeee Meeeeeee: Mee M. Meeee Meeeeeeeee[‌888‌]

Me eee, eeee eeeeeeeee eeeeeeeeeeee eeeeee, eeeeeeeeee eeeeeeee eeeeeeeeeeeee eeeeeeeeee eee eeeeeeeee eee eeeeeee eeeeeee ee eeeeeee eeeeee eee eeee eeeeeeeee eeeeeeeeeeeeeeeeeee eeee eeeeee eeee eeeeeeee (Meeeee 88). Meeee eeeee eeee eeeeeeeeeeee, eee eeeeeeeeeeee-8-ee eeeeeee (MM-eeeeeee) eee eee 8-eeeeee-8M-eeeeeeee-8-ee eeeeeee (MM-eeeeeee) eee ee eee eee eeee eeeeeeee eeeeeeee eeee.[‌888‌] Meee eee eeeeeeeeeeee-8-ee eeeeeee ee eeee ee eeeeeee eee eeeeeeeeee eeeeeeeee ee eeeeeee, eee eeeeeeee ee eeeeee eee M. Meeee eeeeeeeeee, eeeee eee eeeeeeeee. Meeeeeeee, eee eeeeeeeeee eeeeeeee eeeee ee eeeeeeee ee 8-eeeeee-8M-eeeeeeee-8-ee eeeeeeee ee eeeeeeee ee ee eee MeeeeMeeeeeeee eeeeeeeeee.[‌888‌]

Meeeee 88 Meee Meeeeeee Meee Meeeeeeeeeee Meeeeeeeee ee Meeeee-Meeeeeeeee Meeee Meeeeeeeeee[‌888‌]

Me eee eeeeeee eee eeeee, eee eeee eeeeeeeeee eeeeeee eee eeeeeeeee MeeeeMeeeeee eeeeeeee eee eee eeeeee eeeeeeeeee Meeee eeeeeeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeeeeee eeeee ee e eeeeeeeeeeeeeee eeeee. Mee eeeeee eeeeeeeee ee eeeeeeeeeeeee eeeee-eeee eeeeee eeeeee eee eeeeeeeeeee eeee eeeeeee eee eeeeee eeeeeeeeeeeeee ee eee eeeeeeeee β-eeeeee eeeeeee eeeeee eeee eee eeeee eeeeee. Meeeeeeeeee ee eee α-eeeeeeee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeee e eeeeeeeeeeee eee ee eeeeeeeeeeeee eeeeee eeeeee eee eeee eeeeeeee. Meee eeee eeeeeeeee eee ee e eeeeeee eeeeeeee eeeee eeee eeeee eee eee eeee eeeee eeee eee eeeeeee eeeeeeee eeeeeeee, eee eeee eeee eeeeee, eeeeeeeeee eeeee e eeeeeeeeeee eeeeeee eeee eeeeeeeeeeee eeee eeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meee-Meeeeeee ee Meeeeeeeeeee-8-ee Meeeeeee[‌888‌]

Me e eeeeeeeeeee, eee eeeeeeeeeeeee ee eee eeeeeee eeeeeeee eee ee ee eeeeeeeee eeee eeeeeeeeeeeeeee eeeee eeee ee eeeeeee eeeeeeeeeeeeeeee ee eeeee eeeeeeeeeeeeeeeeeeeeee. Meeeeeeeeeee, eee eeee-eeeeeeee eee eeee ee eeeeeeeeee ee ee-eeeeee Meeeeee-eeee eeeeeeeeee eee eeee. Meeee eee eeee Meeeeee-eeee eeeeeeee, ee ee eeeeeeeeee eeee e eeee ee eeeee ee e eeeeeee ee eee eeeeeee eee eee eeeeeeee ee eee eeeeeeeeeee. Mee α-eeeeeeee eeeeeeeee ee eeee eeeeeeeee ee eeee eee eeeeeeeeeee eeeeeee eeee eee eeeeeeee eeeeeeee. Meee, ee eee eeeeeeee ee eee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee eeee, ee eeee-eeeeeeee eeeeee. Me eee ee ee eeeeeee eee eeee eee eeeeeeee ee eeee eeeeeee eeeeeeee eeeeeeeeee eee eee ee eeeeeeeeee eeee eee Meeeeee-eeee eeeeeeee eee ee eee eeeeeeee ee eeeeee eeeeeeeee eeeeee eee eeeeeeee. Meeeeee, eee eeee-eeeeeeee ee eee eeeeeeee ee eee eeeeeee eeeeeeee ee eeeeeeeeee ee eee eeeeeeeeeee eee eee eeeeeee eeeeeeee eee ee eeeeeeeee eeeee ee eee eeeeeeee eeeeeeee eeeeeee eee eeee.

Meeeeee, eee eeeeeeeee eeee-eeeeeeee ee eeeeeeeee eeeeeee eeeeeeee eee eeee ee eeeeeeeeee ee eee eeeeeee eeeeee ee eee eeeeeee eeeeeee. Meeee eee eeee eeeeeeee eeee eeeeeee eeeeeeee (MM-, MM-, MMM-, eee MMM-eeeeeee; eee Meeeee 88), eee eeeeeeeee eeeeeeeeeeee-8-ee eeeeeeee eee eee eeee eeeee ee eeeeeee eeee-eeeeeeee, e.e. ee eeee eeeeeee 88 eeee eeeeeeeee eeee eeeee (Meeeee 88).[‌888‌] 8-Meeeee-8M-eeeeeeee-8-ee eeeeeeee, eeeeeeeeee eee eee eeeee eeee ee Meeeeeeee ee 8888, eeeeeee e eeeeeee eeeeeeeeee ee eeee-eeeeee.[‌888‌] Mee eeeeeeeee eeeeeeeee ee eeeeeeeee 8-eeeeee-8M-eeeeeeee-8-ee eeeeeeee, ee eeeeeeee ee eee eeeeeeeee eeeeeeeeeeee-8-ee eeeeeeee, ee eeeeeeeeee eee ee eee 8-eeeeee eeeeeeeee, eeeee eee eeeeeeeeee eeeeee eee eee eeeeeeeeeeeee eeeeee eeeeee eeeeee eeeeeeeeeeee eeeeee. Meeee eeee eeee eeeeeeeeee, eee eeeeee eeeee eee eeee eeeeeeee eeee e eeee-eeeee eeeeeeeeeee,[‌888‌] eeeee eee eeeeeeee ee e eeeeeee eeeeeeeeeee ee eee eeeeeeeee ee eee eeeeeeeee eeeeeee, e eeeeee eeee eeeee eeeeee eeeeeeeeeeeee eee eeeeeeee eeeeeee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeeeee Meeeeee Meeeeeee ee 88°M[‌888‌]

Meeeeeeeeee 88

Me8 Meeee (%) Mee
88 88
8 >88 [‌888‌]
88 >88 [‌888‌]
88 <8 [‌888‌]

Meeeeee, 8-eeeeeee eeeeeeee (MMM-eeeeeeee) eee eeeeeee eee eeeeeee eeeeeeee eeee eee eeeee eeeeeeeeeee ee eeee-eeeeeeee. Meeeeeee, eeee eee ee eeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeeeee. Meee eeeeeeee, ee eee eeee eeeeeeee eeee eee eeeeeeeee eeee ee e 8-eeeeeee eeeeeee ee eeeeee eee ee eeeee 8 eeeeeee ee eeee eeeeeeeeeee.[‌888‌,‌888‌]

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

Meeee eeee eeee eee ee eee eeeeeeeeee eeee ee eeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeee eeee eee eee eeeeeee eeeee ee eeeeeeee 88 ee eeeeeeee ee eee eeeee eeeeeeeeeee eeee eeeeeeeeee 88M eeee (M)-88 eee 88M eeee (M)-88 (Meeeee 88).

Me e eeeeeeeeeee, eee M/M eeeeeeeeeee ee eee eeeeee-eeeeeeeeee Meeee eeeeeeeeee eeeeeee ee eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeee eeeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeee eeee eee eeeeeeee eeeeeeee. Meeee eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeeeee eeeeeeee ee e eeeeeeee eeeee eee ee eeeeeeeeee ee eee eeeeee ee eee eeeeeee eee eee eeeeeeeeeeeee (Meeeee 88), ee eee ee eeeeeeeee eeee eee eeeeeeeeeee eeeeee ee eeeee eee eeeeeeeeee eee eeeeeeeeeeee eeeeeeee eee M eeeeeeeeeee ee eee eeeeeeee.

Meeeee 88 Meeeeeeee Meeeeeee Meeeeeeee eee eee Meeeee-Meeeeeeeee Meeee Meeeeeeeee[‌888‌‌888‌]

Meee, ee eeeeeeeee eeeee 8-eeeeee-8M-eeeeeeee-8-ee ee eeeeeeeeeeee-8-ee eeeeeeee eee eeeeeeeee ee eeeeeeee eeee eeeeeeeee eeeeeeeee, eee eeeeeeeee eeeee eee ee eeeeeee ee eeeeeee eee eeeeeeeeeeeeeeeee ee eee eeeeeeee eeee (eee eeeeeeeee eee M/M eeeeeeeeeee) (Meeeee 88): e eeeeeeee eeeeeee eee e eeeee eeeeeeeeeeeee (eeeeeee) eeee eeeee eee eeeeee eeeeeeeeee eeeee 88 [eeeeeeeee eee eee-eeeeee eee-88 eee eee M-eeeeee (M)-88] eee ee eee eeeeeeeeee eeeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeeee eeeee 88. Me eeeeeeee, eeeee eeeeeeee eee eeeee eeeeeeeeeeeeee eeee eeeee ee eeee, eeeeeeeeeeee eeeeeeeeee-eeeee eeeeeeeee 88 [eee eeee-eeeeee eeee-88 eee eeee eee M-eeeeee (M)-88 ee eeeeee eeeeeeeeeeeeee]. Me eeee eeeee, ee eee ee ee eeeeeee eee eeee eeeee eeeee eeeeee ee eeeee eeee ee eeeeeeeeee eeeee eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee ee α-eeeeeeee eeeeeeeee ee ee eeeeeeee ee eeeeee eeeeeeeee eeeeeeeee eee eeeeeeeee, ee eeee eeeee, eee eeeeeeee eeeeeeee eee ee eeeeeeee (Meeeee 88).[‌888‌,‌888‌] Meeeeee, ee eeeeee eeee ee eeeee eeee 8-eeeeee-8M-eeeeeeee-8-ee eeeeeeee eeee eee eeeeeee eeeeeee eeeeeeeee eeee eeeeee M/M eeeeee eeee eee eeeeeeeeeeee-8-ee eeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeee ee eee Meeeeeeeeee Meee ee eee Meeeee-Meeeeeeeee Meeee Meeeeeeeee Meeeeeee[‌888‌,‌888‌]

Meeeee 88 Meeeeee ee Meeeeeee eee Meeee ee eee Meeeeeeeeeeeeeeee ee eee Meeeee-Meeeeeeeee Meeee Meeeeeeeee Meeeeeee[‌888‌]

Meeeeeeeeee 88

Me8 Meee Meeeeee Meeee (M/M) Mee
MeMMMM eeeeeee 88:88 [‌888‌]
MeMMMM MMM 88:88 [‌888‌]
MMMMM eeeeeee 88:88 [‌888‌]
MMMMM MMM 88:88 [‌888‌]
MeMMMM eeeeeee 88:88 [‌888‌]
MeMMMM MMM 88:88 [‌888‌]
MMMMM eeeeeee 88:88 [‌888‌]
MMMMM MMM 88:8 [‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeee ee eee Meeeeeee ee Meeeeeeee Meeeeeeeeeee-8-ee Meeeeeee ee Meeeeeeee[‌888‌‌888‌]

Meeeee 88 Mee-eeeeeee Meeeeeeeee ee eee Meeeeeee eee Meeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88M

Meeeeeeeee Meeee (M/M) Meeee (%) Mee
MeMMMM, eeeeeee 8:88 >88 [‌888‌]
MeMMMM, MMM 8.8:8 >88 [‌888‌]
MeMMMM, MMM 88:8 >88 [‌888‌]
MMMMM, eeeeeee 8:8.8 >88 [‌888‌]
MMMMM, MMM 8.8:88 >88 [‌888‌]

Meeeeeeeeee 88M

Meeeeeeeee Meeee (M/M) Meeee (%) Mee
MeMMMM, MMM 8:8 >88 [‌888‌]
MMMMM, MMM 8:8 >88 [‌888‌]
MeMMMM, MMM, MMMM 8:8 >88 [‌888‌]
MeMMMM, MMM, MMMM >88:8 >88 [‌888‌]

Meeeeeee, eeeee eeeee eee eeee ee eeeeeee ee eeeeeeeee, eeeeeeee, ee eeeeee eeeee 8-eeeeee-8M-eeeeeeee-8-ee ee eeeeeeeeeeee-8-ee eeeeeeee eee eeeeeeeee ee eeeeeeee eeee eeeeeeeee. Me eeeeeeee 8-eeeeee-8M-eeeeeeee-8-ee ee eeeeeeeeeeee-8-ee eeeeeeee eee/ee eeee ee α,β-eeeeeeeeeee eeeeeeeee eee eeee ee eeeeeeeeee, eee eeeeeeeeeeeeeeeee ee eee eeeeeeee eeee eee eeee eeeeeee ee eee eeeeeeeeeeeeeeeee ee eee eeeeee β-eeeeee eeeeeee.[‌888‌,‌888‌]

Meeeeeeee β,γ-eeeeeeeeeee eeeeeeeeeeee-8-ee eeeeeeee (e.e., 88) eeeee eeee eeeeeeeeeeeee eeeeeeeee eeeeeeeee ee eeee eee eeeeeeee eeeeeee (e.e., 88) eeee eee ee eeeeeeee M eeeeeeeeeee (Meeeee 88). Meee eee eeee M eeeeeeeee 8-eeeeee-8M-eeeeeeee-8-ee eeeeeeee (e.e., 88) eeeee eeeeeeeeeee eeeeeeeeeee ee M-eeeeeee (e.e., 88) eeeee eeeeeeeee eeeeeeeeee (Meeeee 88). Meee eeeeeee ee eee M/M eeeee ee eee eeeee eeeeee eeeeeee ee ee eee ee eee eeee eeee eee eeeeeeeeeeee β-eeeeeeeeee eeeeeeee eee ee eeeeee eee eeeeeeeeeee eeeeeeeee eeeeeeee ee eee eeeeeeee.[‌888‌] Meeeee, eee ee eee eeee eeeeeeeee ee α-eeeeeeeee eeeeeeee, eee β-eeeeeeeeee eeeeeeee eeeeee eeeeeee eeeee-eeeee eeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeeeeeeeeee eeeeeeeeee eee eee eeeeeeeee. Mee eeeeeeeeeeeee ee eee eeeeeeeeee α-eeeeeeeee eeeeeeeeeeee-8-ee eeeeeee eee eeee eeeeee eeeeeeeeeeeeee (Meeeee 88).

Meeeee 88 Mee Meeeeeeeeee ee β,γ-Meeeeeeeeee Meeeeee Meeeeeee ee eee Meeeee-Meeeeeeeee Meeee Meeeeeeeee Meeeeeee[‌888‌,‌888‌]

Meeeee 88 Meeee-Meeee-Meee Meeeeeee ee Meeeeeeeeee β-Meeeeeeeeeeeee Meeeeeee[‌888‌]

Meeeee eeee eeeeeee eee ee eeee eeeeeeeeeeeee eeeeeee eee eee- eee eee eeee-eeeeeee, eee eeeeeeeeee eeee eee eeeeee eeeeeee eee eee Meeeee eeeeeeeeeeeee ee eee eeee-eeeeee eeee-88 ee eeeeee eeee eee eee eee-eeeeee eee-88, eee ee eee eeeeeeee/eeeeee eeeeeeeeeeee ee M8 eee M8 ee eee eeeeeeeeee eeeeee eee eeeeeeeeeeeeeeee, ee ee eeeeeee eeee eee M-eeeeee ee eeeeee eeeeeeeeeeeeee (Meeeee 88). Meeeeee, ee eee ee ee eeeeeee eee eeeee eeee, eeee eee eeeeeeee ee β,γ-eeeeeeeeeee 8-eeeeee-8M-eeeeeeee-8-ee eee eeeeeeeeeeee-8-ee eeeeeeee ee eeeeeeeee ee eeeeee eeeeeeeee eeeeeeeee eee eeeee eee eeeeeeee eeeeeeee ee eeeee, eee eeeeeee, eeeeeeee eeeeeeeeeeee-8-ee eeeeeeee, eeee eeee ee eeeee eeee eeeeeeee eeeeeeeeeee eeeeeeeee, eeeeeee eee eeeee eeeeeee eeee eeee M eeeeeeeeeeeee.[‌888‌]

Mee eeeee eeeeeeee eeee eeeeee eeee ee α-eeeeeeeee eeeeeee eeeeeee eeeeee eeee ee eeeeeeeeeee eeeeeeee. Me eee eeee eeeee eeee eee eeeeeeeeeee ee eee- ee eeee-β-eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeeeee eee eeee eeee ee eeeeeeeeeeeeeeeee eeeeeee, eeeeeeeeee ee eeeeeee eee β,γ-eeeeeeeeeee α-eeeeeeeee eeeeeee ee eeee ee eee eeeeeeee eeeeeee. Me eeee eeeee, ee eee eeee eeeee eeee eeee eee eeee eee-β-eeeeee eeeeeeeeeeee-8-ee eeeeeee, eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeee, eeeeeeeee eeeeeeeeeeeee eeee eee M-eeeeee.[‌888‌]

Me eeeeeee eeee eeeeeeeeeeeeee eeeeeeeeeee, ee eee eeee eeeeeeee eeee e eeeeee eeee ee eeeeeeeeeeeeeeeeeeeee (eee eeeeeeeeeeee-8-ee eeeeeeee) eeee eeeeeeeeeeeee 88M eee 88M eee eeeee, eeeeeeee eee eeeeeeeeeeee eeeeeeeeee 88M eee 88M, eeeeeeeeeeee.[‌888‌] Meeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeee eeeeeeeeeeeee eeee eeeee eeeeeeeeeeee 88M eeeeeeee eee M-eeeeee (M)-88 eeee eeee ee eeeeee eeeeeee (Meeeee 88). Me ee eeeeeee eeee eee eeeeeeeee eeeeeeeeeee ee eeeeeeeeee ee eee eeeeeeeeeee eeeeeee eeeeeee ee eeeee eeeeeeeee eee eeeeeeeee eeee MM8-eeee eeeeeeeeeee eeeeeeee. Mee eeeeeeeee ee eee eeeeeeeeeeee ee eee eeeeeeee eeee ee eee eeeee eee eeeeeeeeeee ee eeee eeeeeeee eeee eeeeeeee eeee eeeeeeeeeee eeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee M-Meeeeee ee ee MM8-Meee Meeeeeee[‌888‌]

Meeeeee, eee eeeeeeee ee eeeeeeeee β,γ-eeeeeeeeeee eeeeeeee ee eeeeeeeeeee eeeeeeeee eeeeeeeeee e eeeeee eeeeeeee. Meeeeeeeeeee, ee ee eeee eeeeeeeee ee eeeeeee eee eeeeeeeeeeeeee eeeeeee. Me eeeeeee, M-eeeeeee eee eeeeee, eee e eeeeeeee ee eeeeeeee eeeeee ee eeeee M-eeeeeee eee eeeeeeeeeeeeee eeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeee ee β,γ-Meeeeeeeeee α-Meeeeeeee Meeeeeeeeeee-8-ee Meeeeeee eeee ee Meeeeeeeeee Meeeeeee[‌888‌]

Mee eeeeeeeeee eeeeeee eeeeeeeeeeee-8-ee, 8-eeeeee-8M-eeeeeeee-8-ee, 8-eeeeeee (MMM), eee 8-eeee-eeeee-8M-eeeeeeee-8-ee (MMM) eeeeeeee ee eeee 8-eeeeeee eee 8-eeee-eeeee-8M-eeeeeeee-8-ee eeeeeeee eee eeee eeee eeeeeeeee ee eeeeeee eeee-eeeeeeee. Meeeeee, eeee eeeeeee eee eeeeeee eeee eeeeeee M eeeeeeeeeee eee ee eeeeeeeee eeeeee eeeee.[‌888‌,‌888‌]

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

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

Meeeee 88 Meeeeeeeeee ee 8-Meeeeee Meeeeeee ee eee Meeeee-Meeeeeeeee Meeee Meeeeeeeee Meeeeeee[‌888‌]

Mee eeeeeeeeee ee β-eeeeee 8-eeeeeee eeeeeeee ee eeeeeee e Meeeee eeeeeeeeeeeee eeeeeee eee eeeee-eeeee eeeeeeee ee eeee eeeee. Meeee, ee eeeeeeeeeee eeeeeee eee eeeeeeee α-eeeeeeeee 8-eeeeeee eeeeeee, eee eeeeeeee, eee eee eee- eee eeee-β-eeeeee 8-eeeeeee eeeeeee eeeeeee eee ee eeeeeeee eeeeeeeeeee. Meeee eee Meeeee eeeeeeeeeeeee ee eee eee-β-eeeeee 8-eeeeeee eeeeeee eeeeeeee eeeeee eeee eee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeee-eeeeee, eee M-eeeeeee eee eeeeee eeeeeeeeeeeeee.

8-eeee-Meeee-8M-eeeeeeee-8-ee eeeeeeee (MMM-eeeeeeee) eee eeee eeee eeeeeeeee eeeeee eeee-eeeeeeee. Meee ee eeeeeeeeee eee ee eee eeeeeeeeee eeeeee eeeeeeeee eeeeeeeee ee eee eeee-eeeee eeeee eeee eeeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeee eeeeee.[‌888‌]

Meee eeee ee eeeee eeee eeeeeeeee, eeeeeeeee 8-eeee-eeeee-8M-eeeeeeee-8-ee eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeee eeee eeeeeeeeeeeee eeeee M eeeeeeeeeee eeee eee eeeee eeeeeeee. Meeeeee, eeee β,γ-eeeeeeeeeee 8-eeee-eeeee-8M-eeeeeeee-8-ee eeeeeeee eee eeee, M-eeeeeee eee eeeeeeee eeee eeeeeeeee eeeeeeeeeeeee (Meeeee 88). Mee eeeeeee eee eeee eeeeeeee M eeeeeeeeeee eee eeeeeeeeee eee eeee ee eee eee 8-eeeeeee eeeeeeee.

Meeeee 88 Meee M Meeeeeeeeee ee eee 8-eeee-Meeee-8M-eeeeeeee-8-ee Meeeeee Meeeeeee Meeee Meeeeeeeee[‌888‌]

Meeeeeeeeee 88

Me8 Meeee (M/M) Meeee (%) Mee
88:88 88 [‌888‌]
88:88 88 [‌888‌]
8:88 88 [‌888‌]