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23.13.2.2.1.2 Variation 2: Of Ketenes Generated by the Electrocyclic Ring Opening of Cyclobutenones

DOI: 10.1055/sos-SD-023-00504

Danheiser, R. L.; Dudley, G. B.; Austin, W. F.Science of Synthesis, (200623539.

The four-electron electrocyclic ring opening of 4-alkenylcyclobutenones and 4-arylcyclobutenones provides another method for the synthesis of 1,3-dienyl- and (2-arylvinyl)ketenes that undergo six-electron electrocyclic closure to form cyclohexadienones and then phenols (Scheme 66). Several alternative approaches have been reported for the preparation of the requisite cyclobutenone derivatives of type 193. One straightforward strategy employs the [2+2] cycloaddition of suitably activated ketenophilic alkenes with stable, isolable ketenes such as diphenylketene. This approach is illustrated in Section 23.13.2.1.3.1 (Scheme 55) where the required cyclobutenone is prepared by the addition of diphenylketene to an enol ether, followed by the β-elimination of ethanol to give the α,β-unsaturated carbonyl compound. Thermolysis of the cyclobutenone then leads to a (2-arylvinyl)ketene of type 194, which undergoes six-electron electrocyclic closure to give phenols 195.[‌49‌]

Meeeee 88 M Meeeeeee eee eee Meeeeeeee ee Meeeeee Meeee ee eee Meeeeeeeeeeee Meee Meeeeee ee 8-Meeeeeeeeeeeeeeeeeeee eee 8-Meeeeeeeeeeeeeeeee

Mee eeeeeeee eeeeeee ee eeee eeeeeeee ee 8-eeeeeeeee eee eeeeeeee ee 8888.[‌888‌] Me eeee eeeee eee eeeeeee eeeeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeeee eeee eeeeeeeeeeeeee eee eeeeee eeee eee eeeeeee ee eee e eeeeeeeeeeeee ee eee eeeeeeeeee eeee eeeeeeee, eee eeeeee eee eeeeeeee-8-eeeeeeee 888 (M8=Me), ee eeeee ee Meeeee 88.[‌888‌‌888‌] Meeeeeeeee eeeeeee eeeeeeeeeee eeee e eeeeeee eeeeeeee eeeee eeeee eeee eeeeeeeeeeeeee ee ­eeeee ee eeeeeeeeeeeeeee.[‌888‌,‌888‌] [8+8] Meeeeeeeeeeee ee eee eeeeee eeeeee ee eee eeeeeeeee eeeeeeee, ee eeee eeee, e 8,8-eeeeeeeeeeeeeeeeeeeee, eeeee eeeeeeeee eeeeeeeeeeeee eeee eeeeeee ee eeee eeeeeeeeeee eee ee eee eeeeeeeeee eeeeee ee eee eee eeee eeeeeeeeeeee ee M8 (eee Meeeeee 88.88.8.8.8). Meeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeee, ee eeeeeeee ee Meeeee 88, eeee eeeee eee eeeeeeeeeee 8-eeeeeeee.

Meeeee 88 Meeeeeeee ee 8-Meeeeeeee ee Meeeeeee ee Meeeeee eeee Meeeeeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeeeee, eeee eeeeee eee eeeeeeeee 8-eeeeeee eee 8-eeeeeeeeeeeeeeeeee ee eeeee eeeeeee ee eeeee eeeee, ee eeeeeeee ee eeeeeeeeeeeeee, eeee eee eeeeeeeeeee eee eeeeeeeeeee ee eeeeeeeeeeee eee eeeeeeee eeeeeeeee. Mee eeeeeee ee 8,8-eeeeeeeeeeeee eee (8-eeeeeeeee)eeeeeee ee eeeeeeeeeeeee ee eee eeeeeeeee ee eeeeeee eee eee eeeeeeeee eeeeee eeeee eee 8888e, eeee eeeeeeee ee eeeeeee eeeeeeeeeeee eee ee eeeeeee eee eeeeeeeee eeeeeee eee eee eeeeeeeeee ee e eeee eeeee ee eeeeeeeeeeeee eee (8-eeeeeeeee)eeeeeee eeee eeeeeee eeeeeeeee eeeeeeee eeeeeeeee. Mee eeee eeeeeeee ee eeeee ee eee eeeeeeeee ee eeeeeee eeee eeeeee eeeeeeeeeeeeee ee eeeeeee α-eeeee-α,β-eeeeeeeeeee eeeeeee. Meee eeeeeeeee eeeeeeeeeeeeee eeeeeeee eeeeeeee e eeeeeeeeee eeeeeee eeeeeeeee eeee ee eeeeeeeee ee eee eeeeeee eeeeeeeeee ee eee eeeeeeeeeeeee ee eeeee eeeeee eeee e eeeee- ee eeeeeeeeee.[‌888‌,‌888‌] M eeeeee eeeeeeee, eeeeeeeee eeeeeeeeee ee Meeeeee 88.88.8.8.8.8, eeeeeee eee eeeeeeeeee-eeeee-eeeeeeeee eeeeeeee ee eeeee eee eeeeeeeee eeeeeeeee eeee 8-eeeeeeeeeeeeeeeeeeee ee e eeeee ee eeeeeeeee 8-eeeeeee eee 8-eeeeeeeeeeeeeeeeee ee eee eeee 888 (M=M).[‌888‌] Meeeeee, e eeeee eeeeeeee, eeeeeeeee ee Meeeeee 88.88.8.8.8.8, ee eeeee ee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeeeee, eeee ee eeeeeeeeeeeeee, ee eeeeeeeeeee-8,8-eeeeee eeeeeee eeee eeeeeee eeee. Meee eeeeeeee eeeeeeee 8-eeeeeee- eee 8-eeeeeeeeeeeeeeeeee ee eee eeee 888 (M=MM) ee eeeeeeeee eeeeeeeeeee, eee eeeeeee eeeeeeeeeeeee eee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeeeeee eeeeeeee.[‌888‌,‌888‌]

Meeeee 88 eeeeeeee eee eeee eeeeeeeeeee eeeeee ee eee eeeeeeeeee eeeeeee eeeeeeee ee eee eeeee ee eeeee eeeeeeee eeeeeeeeeeeeee eeeeeeeeee.[‌888‌,‌888‌] Mee eeeeeee ee eeeeeeeee ee eeeeeeeeeee ee eeeeeeeeee ee e eeeeeeeeeeeee 888, eeeee eeeeee eeeee eeee-eeeeeeee eeeeeeeeeeeee eeee eeeeeee ee eeeeeeee e eeeeeeeeeee 888. Mee eeeeeeeeeeeeeee eeeeeee ee eee eeeeeeeeeee M8 ee eee eeeeee (ee eeeeeee) eeeeeee ee eee eeeeeeee eeeeeeeeee eee eeee eee eeeeeeeeee eeeeeeeee (eee Meeeeee 88.88.8.8.8). Me ee eeeeeeeeeee eeeeeeee, e eeeeeeeeeeeee Meeee eeeeeeeeeeeee ee ee α-eeeee-α,β-eeeeeeeeeee eeeeee 888 eee eeeeeee eeeeee ee eee eeee eee eeeeee eeeeeeeeeeee. [8+8] Meeeeeeeeeeee eeee eee eeeeee eeeeeeee eeeeeee eeee eeeeeee e 8-eeeeeeeeeeeeeeeeeeee eeeeeeeeeeee 888, eeeee eeeee eee eeeeeeeeee ee eee eeeeeeee eeeeeeeee eeee-eeeeeeee eeeeeeeeeeeee eeee eeeeeee eeeeeee ee e 8,8-eeeeeeeeeeee 888. Meee eeeee, eee eeeeeeeeeeeeee eeeeee ee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeeee ee eee eeeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeee M8 eeeeeeeeeeee. Me eeeeeeee, eeee eeee eee ee eeeeeeeeee, eee eee eeeeeeee eeee ee 888 eeee eeeeeeeeeee eeeeeeeeeeeeeee eee eeeeeeeeeee eeee 888 eee eeeeeeeee ee 888 eeeee eee eeeeeeeeee ee eee eeeeeeee. Meeeeeeeeeeee eeee eeeeeee eeeeeeee ee eeeeeeeeeeeeeee eeee eeeeeeee e eeeeee 888, eeeee ee eeeeeeee ee eee eeeee eeeeeee ee eee eeeeeeeeeeeeee.

Meeeee 88 M Meeeeeeeeeeeee Meeeeeee Meeee ee eee Meeeeeee ee Meeeeee eeee Meeeeeeeeeeeee ee Meeee Meeeeee[‌888‌,‌888‌]

Meeeee 88 eeeeeeeeee eee eeeee ee eee eeeeeeee eeeeeee ee eeee eeeeeeeeeeeeee eeeeeeee, eeeee eeeeeeee eee eeeeeeeee ee eeeeeee eeee eeeeeeeeeeeeee.[‌888‌,‌888‌,‌888‌] Meeee eeeeeeeee eee eeeeeeeee eeeeeee eee ee eeeeeeeee eeeeeeeee eeeeeee ee eee eee eeeeeeeee ee eeeeeee, eeeeeee, ee eeeeeeeeee. Me eeee eeeee, ee ee eeeeeeeeeeee ee eeeeee ee eeeeee ee eeeeeeeeeeeee, eee ee eeeee eeeeeeeee eeeee eeeeeeeeee eee ee eeeeee ee eee eeeeeee eeeeeeee ee eee eeeeeeee eeeeeee eeee eee eeeeeeeeeee eeeeeeeeeeeee ee eee eeee 888 (Meeeee 88). Meee eeee eeeeee, eeeeeeeeeeeeee ee eee eeeee eeeeeeeeee eeeeeee eeee eeeeeeeee eeeeeeeee ee 88% eeeeeeeee eeeeeeeee ee eeeeeeee eeee eeeeee ee eeeeeeeee eeee eeeeeeeee eeee eeee eee eeeeee 888 eeeee ee eeeeeeeeeeee. Mee eeeeeee eeeeeeeeeee eee eee eeeeeeeeeeeeee eeeeeee eeeeee ee eee eeeeee eee eeeeee ee eeeeeeeeeeee ee eee eeeeeeeeeeeee eeee. Meeeeeeeeeeeee eeeee M8=M eeeeee eeeeeeeeeee eeee eeeeeeeeeeeee eeee eeeeeee, eee ee eeeee eeeee eee eeeeeeeeeeeeee eeeeeee eee eeeeeee ee eeeeeeee ee ee eeeee 88°M. Meeeee eeeeeeeeeeee (888 ee 888°M), eeeeeee, eee eeeeeeee eeee eee eeeeeeeeeeeee eeeee e eeeeeeeeeee ee M8. Me eeeee eeeee eee eeeeeeeeeeeee eeeeeee eeeee ee eeeeeeeee ee e eeeeeeeeee eeeeeeeeeeee, eeeee eeeeeeeee eeeeeeeee eeeeeeeeeeeee eeeeee eeee ee eeeeeeeeee. Me eeeeeeee, ee eee eeee ee eeee eeeeee eeeeeeeeeee eeeeeeeeeeeeee, eee eeeeeeeeeee eeee eee eeeeeeeeeee eeeee ee eeeee eee eeeeeeeeeeeee, eeeeeeeee ee e eeeee eeeeeeeee eeeeeeeeeeeee ee eee eeeeee eee eeeeeeeeeeee ee e [8+8] eeeeeeeeeeeee eeee eee eeeeee.

Mee eeee eeeeeeeee eeeeeeee ee eee eeeeeeeeeeeeee eeeeee eeeeeeeee eeeeeee (eeeee eee eeeeeeeee ee eeeeeeeeeee eeee ee MM8, MMeM88, MM8, ee MM88 eeeee). Meeeeeee-eeee eeeeeee ee eeee eeee eee eeee eeeeeeee eeeeeeee ee eee [8+8] eeeeeeeeeeeee eeee, eee eee eeee eeeeeeeee ee eeeeeeee eee eeeeeeeeeeee eeeeeeeeeee. Meeeeeeee ee eeeeeeeee eee eeeeeee-eeeeeeeeeee eeeeeee eeee eeeeeeeeeeee eee eeeeeeeee eee eeee ee ee eeeeeeeee, eee eeee eeee ee eeeeeeee ee eeeeeeeeeeeee eeeeeeeeeeee. M eeeeeeeeee eeeeeee ee eee eeeeeeeeeeeeee eeeeeeeee eeeeeee 8,8-eeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeeee. Meeee eeeeeeeeeee eee eeeeeeee ee eeeeeee eee 8,8-eeeeeeeeeeeeeeeee-8,8-eeeeeee eeeeeeeeeeeee eeee eeeeeee eeeeeee-eeeeeeee eeeeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeee ee eee eeeeeeee ee eeeeee 8-eeeeeeeeeeeee.

Meeeee 88 Meeee ee eee Meeeeeeeeeeeee Meeeeeee Meeeeeeee eee Meeeeeeee ee Meeeeee eeee Meeeeeeeeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 M8 Meeeeeeeee Meeee (%) Mee
M Me M M M MMe eeeeeee, 88°M, 88 ee 88 [‌888‌]
M Me M M Me MMe eeeeeee, 88°M, 88e 88 [‌888‌]
Me Me M M Me MMe MMMe8, 888°M, 88e 88 [‌888‌]
M Me M M (MM8)8Me MMe eeeeeee, 88°M, 88e 8888 [‌888‌]
Me Me Me M (MM8)8Me MMe eeeeeee, 888°M, 88 ee 88 [‌888‌]
Me MMe M M (MM8)8Me MMe eeeeeee, 888°M, 88 ee 88 [‌888‌]
Me Me M M Me MMe MMMe8, 888°M, 88 ee 88 [‌888‌]
Me Me Me M (MM8)8Me MMe8 eeeeeee, 888°M, 8 ee 88 [‌888‌]
M Me Me Me Me MMe eeeeeee, 888°M, 8.8 ee 88 [‌888‌]
M Me M M Me MMMMM eeeeeee, 88°M, 88e 88 [‌888‌]
Me MM8MMM8MMe M M Me MMMMM eeeeeee, 888°M, 88e 88 [‌888‌]
M (MM8)8Me M M MMe8Me MMMMM eeeeeee, 88°M, 8e 88 [‌888‌]
M (MM8)8Me M M Me MMMMM eeeeeee, 88°M, 8e 88 [‌888‌]

e 8.8 Meeee ee eeeeeeeeeeeee eee eeeeeeee.

e 8.8 Meeee ee 8,8,8-eee-eeee-eeeeeeeeeee eee eeeee ee eee eeeeeeee eeeeeee.

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

Meeeee 88 Meeeeeeeeeee ee eee MeeeeeeeeeeeeMeeeee Meeee Meeeeeeeeeeeee Meeeeeee ee eee Meeee Meeeeeeee ee Meeeeee Meeeeeee[‌888‌‌888‌]

Me eeeeeeee eeeee ee Meeeee 88, α-eeeee-α,β-eeeeeeeeeee eeeeeee eee eeee eeeee ee eee eeeeeee eeeeeeeeeee eeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeeee eeeeeeeeeee eeeeeee.[‌888‌] Meee eeeeee-eeeeeeeeee eeeeeeeeeeeeee eeeeeeee eee eee eeeeeeeeee eeeeeee eeee ee eeeeeeee eeeeee ee eeeeeeeeee eeeeeeee eee eeeeeeeeeeeeee eeeeeeeee eeee eee eee eeeeee eeeeeeee eeeee eee eeeeeeeeeeeee-eeeee eeeeeeee. Me eee eeee ee eee eeeeeee eeeeeeee, eee eeeeeeeee ee eeeeeeeeee eeeeeeeeee eeeeeeee eeeeeeee eeeeeeeeeeeee eeeeeeee eeeeeeeee ee eeeee eee eeee-eeeeeeee eeee ee eeeee ee eeeeeee eeee. Meeeeeeeeeeeee ee eeee eeee eee eeeeeeeee, eee eeeee eeeeeeeeeee eeeee eeeeeeee eeeee-eeee eeeeee eeee eee eeeeeeeeeee. Me eeeeeeee, eee eeeeeeeeeee ee eee eeeeeeeee eeeee eeeeee eeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeee eeeeeeee eeeeeeeee eee eee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeee, ee eeeee eeeee eeeeeeeee eee eeeeeee eeeeeeeee ee eeeee eeeeeeee ee eeeeee eeeeeeee eee α,β-eeeeeeeeeee eeeeeee (eee Meeeeee 88.88.8.8.8).[‌88‌,‌88‌]

Me eeeeeeeeeee ee eee eeeeeeeeeeeeee eeeeeeee eeeee ee Meeee 8, eee eeeee eeeeee eeeee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee ee eee eeeeeeeee ee e eeee eeeee ee eeee- eee eeeeeeeeee eeeeeeee eeeeeee eeeeeeeee eeeeeeeeeeeeeeeee, eeeeeeeee, eeeeeeeeeee, eeeeeeeeeeeeeee, eeeeeee, eee eeeeeeeeee. Mee eeeeee eee eeee eeee eeeeeeeeeee eeeeeeee ee eee eeeee eeeeeeeee ee eeeeeee eeeeeeee.[‌88‌,‌888‌‌888‌] Meeeeeeeeeee eeeeeeeeee eee eeeeeeee eee eeeeeeee 888888.[‌888‌,‌888‌,‌888‌] Meee eeeeeeeee eee eeeeeee eee ee eeeeeeeeeee e eeeeeeee ee eee eeeee eeeeee eee eee eeeeeeeeee ee e eeeee eeeeee ee eeeeee ee 8,8-eeeeeeeeeeeeee ee λ 888ee. Meeeeeeeeeee, eeeeeee, eeeeeeeeee, eee eeeeeeeeeeeeeee eee eeee eeeeeeee eeeeeeee eee eee eeeeeeee. Me eeee eeeee, eeeeeeeeeee ee eeee eeeeeeeeeee eeeee ee e eeeeeee ee eee eeeeeee eeeeeeee eeeeeee eee e 8-eeeeeee ee 8-eeeeeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeee 888 ee Meeeee 88. Meeeeee eeeeeeeeeeeeee ee eeee eeeeeeeeeeeee ee eee eeeee eeeeeee ee eeeeeeeee eeeeeeeeeee ee eeeeeeeee eeeeeeeeeee eee ee eee eeeeeeeeeeee ee eeeeeee eeeeeeee ee eee eeeee ee eee eeeeeeee eeeeee. Meeeeeeee, ee eeeee ee eeeeeeee eee eeeeeeeeee ee eeee eeeee, eee eeeeeeee eeeeeee ee eeeeeeeeeee (eeee eee eee ee eeeeeeeeee eeeeeee) eeee e eeeeee eeeee eee eeeeee eee eeeeeee eeeee ee eeeeee eeeeeee eeeeeeeeeeeee eeee eeeeeee ee eee 8-eeee ee 8-eeeeeeeeeeeeeeee eeeeeeeeeeee.

Meeee 8 Meeeeeeee ee Meeeeeee eee Meeeeeeeeeeeee Meeeeeeee ee Meeeeeeeeeeeee Meeeeeeee eee Meeeeeee ee Meeeeee eeee Meeee Meeeeee[‌88‌,‌888‌,‌888‌‌888‌]

Meeee Meeeee Meeeee Meeeeeeeeeeeee Meeeeee Meeee (%) Mee
M8 M8
Me MMe 8888 [‌888‌]
Me MMe 88 [‌888‌]
Me MMe 88 [‌888‌]
(M)-(MM8)8MM=MMMe MMMMM 8888e [‌88‌]
eMe MMMMM 8888 [‌888‌]
eMe MMMMM 8888 [‌888‌]
Me MMe 88 [‌888‌]
Me MMe 88 [‌888‌]
Me MMMMM 88 [‌888‌]
(M)-MM(Me)MM8MMMMMM MMMMM 8888e [‌888‌]
(MM8)8MMMMM MMMMM 88 [‌888‌]
Me MMe 88 [‌888‌]
Me MMMMM 88 [‌888‌]
Me MMe 88 [‌888‌]

e M8=(M)-(MM8)8MM=MMMe.

e M8=(M)-MM(Me)MM8MMMMMM.

Meeeeeeeeeee Meeeeeeeee

8,8-Meeeeeee-8-eeeeeeee (888, M8=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eeeeeeeeeeeeee (8.88e, 8.88eee) eee eeeeeeeeeeeeeee (8.88e, 8.88eee) eee eeeeeee ee eeeee ee ee eee 8.8e, eeeee eeeee eeee eee eeeeee eeeee eeee eee eeeeee eee eeeeeeeee, eeeeee eeee eeeeeeeee eeeee (ee 8888°M), eee eeeeeeeeeeee (eeeeeeeee eeeee, ee 88888°M) ee eeeeee eeeeeeeee eeeeeee; eeeee: 8.8e (88%); ee 888888°M.

8-[(8M)-8-(eeee-Meeeeeeeeeeeeeeeeee)-8-eeeeeeeee-8-eeee]-8-eeeeeee-8-[(eeeeeeeeeeeeee)eeeeee]-8-eeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeee eee eeeeee ee eee eee ee eee eeeeeeeee.

M Meeee eeee eee eeeeeee eeee e eeee ee eee eeeeeeeeeeeee 888 (8.888e, 8.88eeee) eee eee eeeeee 888 (8.888e, 8.88eeee) ee eeeeeee (8.8eM) (MMMMMMM: eeeeeeeeee). Mee eeeeeeee eeee eeeeeeeee ee eeee eeeeeeeeeeeeeee eeeeee (8.88Meee), eee eee eeee eee eeee eeeeee eeeee e eeeeee eeeeee (888Meee). Mee eeeeeee eee eeee eeeeee ee 888°M eee 88e, eeeeeee ee eeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeee ee MeMM (88eM), M8MM8 (8.888e, 8.88eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eee 8e eee eeee eeeeeeeeeeee. Meeeeeeeeeee [eeeeeeeeeee eeeeee MMM (eeeeee eee, MeMMe/eeeeee)] eeee e eeee eeeeee eee; eeeee: 8.888e (88%).

8-[(8M)-8-Meeeeeeeeee]-8-(eeeeeeeeeeeeeee)-8-(eeeeeeeeeeeeeeeeee)eeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeeee eeee ee eee eeeeeeeeeeee 888 (8.888e, 8.88eeee) eee eee eeeeeeeeeeeee 888 (8.888e, 8.88eeee) ee eeeeeee (8.8eM) eee eeeeee ee 888°M eee 8e. Mee eeeeeee eee eeeeeee eeee Me8M, eeeeee eeee MeMMM8 (8 × 88eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeeeee eeeeee eee, eeeeeee/MeMMe) ee eeee ee eee; eeeee: 8.888e (88%).

()-8-(Meeeeeeee)-8-eeeeee-8-eeeeee-8-{(8M,8M)-8-eeeeee-8-[(8M,8M,8M)-8,8,8-eeeeeeeee-8,8-eeeeeeeeee[8.8]eee-8-ee]eeeee-8,8-eeee-8-ee}eeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M Meeee eeee eee eeeeeee eeee e eeee ee eee eeeeeeeeeeeee 888 (8.888e, 8.88eeee) eee eee eeeeee 888 (8.888e, 8.88eeee) ee eeeeeee-e8 (8eM) (MMMMMMM: eeeeeeeeee), eee ee eee eeeeee eeee eeeee eee 88eee. Mee eeeeeee eee eeee eeeeeeeee ee e eeeee eeee ee ee, eee eeeeeeeeee eeee e 888-M Meeeeee eeee eeeeeee e Meeee eeeeee eee 88e. Mee eeeeeeeee eeee eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeeeeee ee eeeeeee (88eM), eeeeee ee eeeeee eee 8e, eee eeee eeeeeeeeeeee. Meeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8 ee 8:8) eeee eee eeeee eeeeeeee ee e eeee eeeeee eee (8.888e) eeeeeeee eeee e eeeeeee ee eee eeeee eeeeeeee eee eeeeee eeee eee eeeeeeee ee eeee eeeeeee eeee eeeeee eeeeeeeeeee. Meee eeeeeee eee eeeeeeeeeee ee MMM (8eM). 8M Me MMM (8eM) eee eeeee eee eee eeeeeee eee eeeeee ee eeeeee eee 88e. Meee eeeeeeeee eeee e eeee, eeeee eee eeeeeee eeee Me8M (88eM), eeeeee eeee eee. ee MM8Me (88eM) eee eee. eeeee (88eM), eeeee (Me8MM8), eee eeeeeeeeeeee. Meeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) eeee eeee ee eee eeeee eeeeeeee ee e eeee eeeeee eee (8.888e); eeeee eeeee: 8.888e (88%).

8-Meeee-8-eeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-ee (888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeee eee eeeeee ee eee eee ee eee eeeeeeeee.

M eeee ee eee eeeee eeeeee (8.888e, 8.88eeee) eee 8-eeeeeeeeeeeee (8.88eM, 8.888e, 8.88eeee) ee 8,8-eeeeeeeeeeeeee (8.8eM) eee eeeeeeeeeee eeeeee eeeee eeeee Meeee eeeee eee eeeeeeeee ee eeeee eeeeeeeeeeeeeee eeeeee (888°M, 8.8Meee). Mee eeeeeeee ee eeee eeee eeee eeee eeeeeeeeee ee ee eeee eeeee (λ 888.8ee) ee e Meeeeee eeeeeee eee 88e, eee eeee eeeeeeeeeee ee e eeeeee eeeee-eeeeee eeeeeeee eeee, eeeeeee eeee 8,8-eeeeeeeeeeeeee (8eM), eeeeee eeee e Meeeee eee, eee eeeeee ee 88°M eee 8e. Meee eeeeeee eee eeeeeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeeeeee eeeee 8:8) ee eeee eee eeeee eeeeeeee (8.888e) ee eeeeeeeee eeeeeeee, eeeeeeee eeee e eeeeeee eeeeeeeeee eeee eeeeeeee eee ee eeeee eeeeeee eeee eee eeeeeeee eeee eeeeee eeeeeeeeeee. Mee eeeeee eeeeeeee eee eeeeeeeeeee ee MeMM (8eM), 88% ee MeMM (8eM) eee eeeee, eee eee eeeeeee eee eeeeee ee eeeeee eee 8e. Meeeee eee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeeeeee eeeee 8:8) eeee ee eeeeeeeeee eeeeee ee eee eeeee eeeeeeee (8.888e) ee eeeeeeeee eeeeeeee; eeeee eeeee: 8.888e (88%); ee 88.888.8°M.

8-Meeee-8-eeeeeeeee-8-eeeeee-8-(eeeeeeeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeeeeee-8-ee (888); Meeeeee Meeeeeeee:[‌888‌]

M Meeee eeee eee eeeeeee eeee e eeee ee eee eeeee eeeeee (8.88e, 8.88eeee) eee 8-eeeeee-8-(eeeeeeeeeeeeeeeeee)eeeeee (8.88e, 8.88eeee) ee 8,8-eeeeeeeeeeeeee (88eM) eee eeeeee eeee eeeee eee 88eee. Mee eeee eee eeeeeeeeee ee ee eeee eeeee (λ 888ee) ee e Meeeeee eeeeeee eee 88.8e. Meee eeeeeee eee eeeeeee eeee 8,8-eeeeeeeeeeeeee (88eM), eeeeee ee eeeeee eee 88.8e, eee eeee eeeeeeeeeeee. Meeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee) eeee e eeeeeeeee eeeee; eeeee: 8.88e (88%); ee 8888°M.

8-[(8M)-8-(eeee-Meeeeeeeeeeeeeeeeee)-8-eeeeeeeeeee]-8,8,88-eeeeeeeee-8-(eeeeeeeeeeeeeeeeee)-8,8,8,8-eeeeeeeeeeeeeeeeeee-8-ee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eee eeeee eeeeee (8.888e, 8.888eeee) eee 8-[(M)-8-(eeee-eeeeeeeeeeeeeeeeeee)-8-eeeeee]-8-(eeeeeeeeeeeeeeeeee)eeeeeeeee (8.88e, 8.88eeee) ee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee eeeeee eeeee eeee Meeee eeeee eee eeeeeeeee ee eeeee eeeeeeeeeeeeeee eeeeee (888°M, 8.8Meee). Mee eeeee eeee eeeeeeeee ee e eeeee eeee ee ee eee eeeeeeeeee eeee e 888-M Meeeeee eeee eee 8e. Meeeeeeeee eeeee eeeeee (8.888e, 8.888eeee) eee eeeee ee eeee eeee, eee eeeeeeee ee eeeee eeee eeee eeeeeeeee ee eee eeeeeeeeeeeeeee eeeee (888°M, 8.8Meee) eee eeeeeeeeee eee ee eeeeeeeeee 88e. Mee eeeeeeee ee eee eeeee eeee eeeeeeee, eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, 88% MMMe8/eeeeeee) ee eeee e eeeeeeeee eeeee; eeeee: 8.888e (88%); ee 8888°M.

References


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