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1.4.10.2 Rhodium–N-Heterocyclic Carbene Complexes as Catalysts for Hydroformylation

DOI: 10.1055/sos-SD-223-00239

Trzeciak, A. M.Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis, (20161449.

Heterocyclic mono(thione)–, trans-bis(thione)–, and cis-bis(thione)–rhodium complexes have been tested in the hydroformylation of hex-1-ene at 80 °C and elevated pressure (4 MPa) to give a mixture of linear and branched aldehydes 5 and 6, respectively. They show better catalytic properties than the NHC analogues. For example, the catalytic productivity of carbene complexes 1 and 2 is ca. 60%, whereas the thione complexes 3 and 4 give the aldehyde products with 100% conversion (Scheme 6).[‌23‌] The addition of triphenylphosphine to carbene complexes 1 and 3 gives complexes 2 and 4, respectively. The presence of a phosphine in the coordination sphere of rhodium leads to an increase in the linear/branched ratio with respect to the complexes without phosphines. A large amount of isomerization products are formed in reactions with complexes 1 (38%) and 2 (44%).

Meeeee 8 Meeeeee–MMM/Meeeeee–Meeeee Meeeeee Meeeeeeee Meeeeeeeeeeeeeee ee Mee-8-eee[‌88‌]

Meeeeeeeeee 8

Meeeeeee Meeeeeeeee (%) Meeee (8/8) Mee
8 88 8:8.8 [‌88‌]
8 88 8:8.8 [‌88‌]
8 888 8:8.8 [‌88‌]
8 888 8:8.8 [‌88‌]

Mee eeeeeeeeeeeeeeee ee eee-8-eee ee 888 °M eee 88 eee, eeeee eeeeeeeeeeeeeeeeeee-8-eeeeeee-eeeeeee eeeeeee eeeeeeeee 8 eee 8, eeeee e eeeeeee ee eeeeee eee eeeeeeee eeeeeeeee 8 eee 88, eeeeeeeeeeee, eeee e eeeeee/eeeeeeee eeeee ee 8.8:8 eeeee 8 eeeee (Meeeee 8),[‌88‌] eeeeeeee eeeee eeee ee eee eeeee ee eee eeeeeeee (eeeee 8.8:8). M eeeeeeeeee eeeeeeeeee ee eee eeeeeeee eeee ee eeeeeeee eeee eeee eeeee eeeeeee–MMM eeeeeee 8 ee eeee eeeeeee ee eeeeeee eeeeeee 8. Mee eeeeeeee eeee ee eeeeeee ee ee. 8.8 eeeee eee, eeeeeeeeeeeeee, eee eeeeeeee eeeeeeeee (MMM) eeeeeeeee eeee ee. 888 e−8 ee 8888 e−8. Me eeeeeeee eeeeeeeeee ee eee-8-eee eee eeeeee/eeeeeeee eeeee ee ~8.8:8 eee eeee eeeeeeee 8 eee 8.

Meeeee 8 Meeeeeeeeeeeeeee ee Mee-8-eee eeee Meeeeee–Meeeeeeeeeeeeeeeeee-8-eeeeeee Meeeeeeee[‌88‌]

Mee eeeeeeeee eeeeeeee ee e eeeeee ee eeee(eeeeeeeeeeeeee)eeeeeee–MMM eeeeeeeee [MeM(MMM)(eee)], eeeee eee MMM eeeeee ee eeeee ee eeeeeeeee (eeeeeee 88), eeeeeee (eeeeeee 88), ee eeeeeeeee (eeeeeee 88), eee eeee eeeeeeee ee eee eeeeeeeeeeeeeeee ee eee-8-eee (ee 88 eee M8/MM) ee eeee eeeeeeee 8 eee 88. Mee eeeeeee eeeeeeee eeeeeeeee (8888 e−8) eee eee eeeeeee eeeeeeeeee (88.8 %) eee eeeeeeee eee eee eeeeeee eeee eee eeeeeee eeeee, eeeeeeeee-eeeee MMM eeeeeee 88 (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeeeeeeeeee ee Mee-8-eee Meeeeeeee ee Meeeeee Meeeeee–MMM Meeeeeeee[‌88‌]

Meeeeeeeeee 8

Meeeeeee MMM (e−8) Mee
88 8888 [‌88‌]
88 8888 [‌88‌]
88 8888 [‌88‌]

Mee eeeeeeee ee eeeeeeee eeee e eeeeeeee ee eee eeeeeeee-eeeeeeee eeeeeeeeee ee eee MMM eeeeee eee ee eeeeeeeee ee eeeeeeeeeee eee eeeee eeeee ee eee eeeeeeeee eeeee. Meee, eee eeeeeeeee ee ee eeeeeee eeeeeee–π-eeeeee eeeeeee ee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeee e eeeeeee–eeeee eeeeeee. Meee eeeeeeeee eee ee eeeeeeeeeee ee eeeeee e eeeee eeeeeeee eeeeeee ee eeeeeee, ee eeeeeeee ee eee eeeeeeeeeeee MMM eeeeee. Meeeeeeeeeeee (eeeeee/eeeeeeee eeeeee) eee eeeeeee eee eee eeeeeee eeeeeeeee, eeeeeee eeee 8.8 ee 8.8 ee eee eeeeeeeee ee eee eeeeeeee eee eeeeeeeeee ee ee. 8.8–8.8 eeee eeeeeeee ee eeeeeeeeee. Meeeeeeeeeeee, eeeee eeeeeeeeeeee eeee ee eeeeeeeee ee eee eeeeeeeeeee eee eee eeeeee eeeeeee ee eeee eeeeee ee eeeeeeee ee ee e eeeeeeeeeeeeee eeeeeee [MeM(MM)8(MMM)] eeeeee ee eeeee ee Meeeee 8.[‌88‌] Me eeeeeeeee eeeeee eeee ee eee eeeeeeee eee eeee eeee eeeeeeee ee eee eeee ee eeeeeeeeeeeeeeeeeee-8-eeeeeee MMM eeeeeee.[‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeee–MMM Meeeeeeee eeee Meeeee Meeeeeee eee Meeeeeee[‌88‌]

M eeeeeee eeeeeee eeee ee eeeeeee-eeeeeeeeeeeeee MMM eeeeee eeeee eeeeeee eeee eee σ- eee π-eeeeeeee (eeeeeee 88) eeeee eeee eeeeeeee ee eee eeeeeeeeeeeeeeee ee eee-8-eee ee eeee eeeeeeee 8 eee 88. Mee eeeeeee eeeeee/eeeeeeee eeeee ee 8.88:8 ee e eeeeee ee eeeeeeeeeeeeeeee ee eeeeeeee eeeeeee eeeeee ee eeeeeeeee eee-8-eee eeeeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeeeee ee Mee-8-eee Meeee e Meeeeee Meeeeee eeee ee Meeeeee-Meeeeeeeeeeeee MMM Meeeee[‌88‌]

Meeeeee–MMM eeeeeeeee eeee eeeeeee eeeeeeeeeee eeeeeee [Me(MMe)(MMe)(MM)8 eee Me(MMe)(MMe)8(MM)] eee eeeeeeee ee eeeeeeee ee eee eeeeeee eeeeeeeee [{Me(MMe)(MM)8}8] eeee eee MMM eeeeee [MMe; 8,8-eee(8,8-eeeeeeeeeeeeeeeee)eeeeeeee-8-eeeeeee].[‌88‌] Meeee eeeeeeeee eee eeee ee eee eeeeeeeeeeeeeeee ee eeeeeee ee eeeeeeeee eeeeeeee ee eeee eee eeeeeeee 88 eee 88, eeee eee eeeeeee eeeeeeeeeee eee eee eeeeeeee eeeeee (eeeeeeee/eeeeee eeeee >88:8) eeeee eeeee ee eeeeeee eeee Me(MMe)(MMe)(MM)8. Mee eeee eeeee, 88%, ee eeeeeeee ee 88 °M eeeee 88 eeeee (eeee 88 eee M8/MM) eeeee eee eeee eeeeeeee (Meeeee 88). Me eee eeeeeeeeeeeeeeee ee eeeeeeee eeeeeeeee eeeeeee, e eeeeeeee eeeeeeeee ee ee ee 888 e−8 ee eeeeeeee; eeeeeee, eee eeeeeeee/eeeeee eeeeeeeeeee ee eee, e eeeeee eeeee eee eeee eeeeeeeeee ee eee eeeeee eeee ee eee MMe eeeeee.

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeee Meeee e Meeeeee–MMM Meeeeee Meeeeeeeee ee Meeeeee Meeeee[‌88‌]

Meeeeeeee eeeeeee 88, eeeeeeee ee eee eeeeeeee ee eeeeee(eeeeeeeeeeeeee)eeeeeee(M) eeeee [{MeMe(eee)}8] eeee 8,8-eee(8-eeeeeeeeeeeeeeee-8-ee)eeeeeeee eeeeeeeee, ee eeee ee eee eeeeeeeeeeeeeeee ee eeeeeee ee 88 °M eee 88 eee eeeeeeee ee eeee eeeeeeee 88 eee 88 (Meeeee 88).[‌88‌] Meeeeeeeeee eeeeeeee eeee eeeee, eeeeeee eeeeeeee eeeeeeeee ee eee eeee eeeeeeee; eeeeeee, eee eeeeeeeeeeeeeeee ee eee-8-eee eeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeee eee eeeeee eeeeeeee [eeeee (eeeeee/eeeeeeee) 88:88]. Me eeeee ee eeeeeeee eee eeeeeeeeeeeee eeeeee eeee ee eee eeeeeeee, e eeeeeeeee eee eeeeeee eeee eeeeeeee/eeeeee eeeeeeee (88 eee) eee ee eee eeeee eeee eeeeeeeeeeee ee eee eeeeeee eeeeeee ee eeeeeeeeee, eee eeeeeeeeeeeeee ee eeeeeeeeeee ee eeeeee eeeeeeee. Mee eeeeeeeeee eeeeeeee, eee eeeeeeeee eeeeeeee eeeeeee 88 eeee e eeeeeeeee MMM eeeeee eee eeee; eeeeeee, eee eeeeeeee ee eee eeeeeeeeeeeeeeee ee eeeeeee ee eeeeeeeeee eee eeee eeeeeeeeee eee eeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee eeeeeee eee eeeee eeeeeee.[‌88‌]

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeee Meeee e Meeeeeeee Meeeeee Meeeeeee Meeeeeeeee e Mee(MMM) Meeeee[‌88‌]

Meeeee eeeeeeeee eee(MMM) eeeeeee eeee M8 eeeeeeee eeee eeee eeee eee eee eeeeeeeeeee ee eeeeeee eeeeeeeee ee eeee 88, eeeee eeee ee eeee eeee eeeeee ee eee eeeeeeeeeeeeeeee ee eeeeeee ee eeee e eeeeeee ee eeeeeeee 88 eee 88 (Meeeee 88).[‌88‌] Meeee eeeeeeeee eee eeeeeeeee ee 88–888 eee eee 88 °M eeee 88 eeeee eeee e eeeeeeee eeeeeee ee 8.8 eee%. Mee eeeeeeee/eeeeee eeeeee eee eeeeeee eee eee eeeeeeeee eeeeeee (~88:8). Meeeeeee ee eee eeeeeeeee eeeeeee eee eee eeee ee eeeeeeeeee eeeeeeeee eeee eee ee eee eeeeeeeeee eeee e eeeeeeeeeeeeee eeeeeee [MeM(MM)8] ee eee eeeeeeeeeeeee eeeeee eeee. Meee eee ee eeeeeeeee ee eeeeeeeeeee ee eee MMM eeeeee eee eeeeeeeee eeeeeeeeeee ee [MMM-M]+ eeee eee eeeeeeeeeeee eeeeee ee eeeeeee.

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeee Meeee e Meeeeee Meeeeee Meeeeeeeee e M8 Meeeeeeee Meeeee Mee(MMM) Meeeee[‌88‌]

Meeeeeeee eeeeeee eeeeeee eeeeeee eee eeee ee eeeeeee eeeeeeeee ee eeee 88, eeeee eeee eeee eeeeee eee eee-8-eee eeeeeeeeeeeeeeee (Meeeee 88).[‌88‌] Mee eeeeeee eeeee ee eeeeeeeee ee eeeeeeee ee e eeeeeeee ee eeeeee eeee 88 eee. Mee eeeeeee, ee 88 eee, e 88% eeeee ee eeeeeeeee ee eeeeee eeee e eeeeee/eeeeeeee eeeee ee 8.88:8 eeeee eeeeeeee 88 (Me8 = 8,8-eMe8M8M8) eeeee eee eeee eeeeeeeeeee [eeeee (eeeeee/eeeeeeee) 8.88:8] ee eeeeeeee eeee e eeeee ee >88% ee 88 eee eeeee eee eeee eeeeeeee. Meeeeeeeeee, ee eeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeee ee eeeeeeee ee eeee eeeeee. Me eeeeeeee, eeeeeee eeeeeee 88, eeee ee eeeee-eeeeeeeeee M-eeeeeeeeeeee eeeeeee eeeeeeeee eeeeee, eeeeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeee ee eee-8-eee eeeee eeeeee eeeeeeee/eeeeeeee (88:88) ee e eeeeeeee ee >88 eee. Mee eeeeee/eeeeeeee eeeee ee eeeeeeee 8 eee 88 eeeeee eeee 8.8:8 ee 8.8:8.[‌88‌]

Meeeee 88 Meeeeeeeeeeeeeee ee Mee-8-eee Meeee Meeeeee Meeeeeeee Meeeeeeeee Meeeeeeee Meeeeee Meeeeee Meeeeee eee Meeee-Meeeeeeeee MMM Meeeeee[‌88‌,‌88‌]

Meeeeeeeeee 88

Me8 Meeeeeee (eee) Meeee (Meeeee/Meeeeeee) Meeee (%) ee 8 eee 88 Mee
8,8-eMe8M8M8 88 8.88:8 88 [‌88‌]
8,8-eMe8M8M8 88 8.88:8 >88 [‌88‌]

Meeeeee eeeeeee 88 eeeeeeeeee e eeeeee MMM eeeeee eee eeee eeee ee eee eeeeeeeeeeeeeeee ee eeeeeee eeee eeeeeeee/eeeeee eeeeeeee (8:8; 88 eee) ee eeee e eeeee ee 88% ee eee eeeeeeee eeeeeeee 88 eeee ee eeeeeeeeeeee eeeeee ee 88% (Meeeee 88).[‌88‌] Meee eeeeeeeeeeeeeeeeee ee eeeee ee eeee eeeeee, eee eeeee eee eee eeeeeeee eeeeeee eeeeeeeee ee 88% eeeee ee eee eeee eeee eee eeeeeeeeeeee eeeeee eeeeeeeee ee 8%. Meeeeeee eee eeeeeeee eeeeeeeeeeeeeeeeee ee eeeeee, ee ee eeeeeeeeeee eeeeeee ee eee eeeeee MMM eeeeee.

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeee Meeee e Meeeeee Meeeeee Meeeeeeeee e Meeeee MMM Meeeee[‌88‌]

Meeeeeeeeee 88

Meeeeeee ee (%) Meeee (%) ee 88 Mee
88 88 [‌88‌]
Me8M 8 88 [‌88‌]

Me eeeeeee, eeeeeeeeee eeeee eeeeeeeeee eee eeeeee ee eeeeeee e eeee eeeee ee eeeeeeeeeeeeeeee eeeeeeee eeeee eeeeeee—MMM eeeeeeeee.[‌88‌,‌88‌] Meeeeeee, eeeeeeee eeeeeeeeeee ee, ee eeee eeeee, eeeeeeeeeeeeee eee ee eeeeeeeee ee eeeee ee eeee eeeeeeee ee eeeeeeeee eeeeeee eeeeeeeeee eee-eeeeeeee eeeeeee eeeeeeeee. Meee, eeeeeee eeeeeee eeee eeee eeeeeeeeee ee eeeeeee eee eeeeeeee ee eeeee eeeeeee, eeeeeeeeee eeee ee MMM eeeeee eee e eeeeeeeeee eeeeee. Me eee eeeeeee, eeeeeee eeeeeee eeeeeeeee eeeeeeeeee MMM eee eeeeeeeeeeeeeeeeee eeeeeee [MeMe(MMM)(MMe8)8 eee MeMe(MMM)(MM)(MMe8)] eeee eeee eeee eee eee eeeeeeeeeeeeeeee ee e eeeee ee eeeeeeee.[‌88‌] Meeee e eeeeeee ee eeeeeeee/eeeeee eeeeeeee (8888 eee) ee 88 °M, eee eeeeeeee eeeeeeee ee eeeeee ee eee eeee eeeeeee eeee e eeeeeeee/eeeeee eeeee ee eee eeeee 88:8–88:8 eeeeeeeee ee eee eeee ee eeeeeeeeeee ee eee eeeeee eeee ee eee eeeeeee. Mee eeeeeee eeeeeeeeeee ee eeeeeeee eee 8-eeeeeeeeeeeee, eeee e eeeeeeeeee ee 88%. Mee eeeeee ee eeeeee eeeeeeeee ee eee eeeeee eee eeee eeee eeeeeee [eeeee eee eeeeeeee MeMe(MMM)(MM)(MMe8)] eee ee eeeeeeee ee eeeeeeeeee eeee 88% eeeeeee eeeee eeeeeeeee ee 88% eeee e eee-eeee eeeeee ee eeeeeeee. Me eeee ee eeeee eeeeeeeeeee, eee eeeeeeee/eeeeee eeeeeeeeeee ee eeeeeee [eeeee (eeeeeeee/eeeeee) 88:8–88:8].[‌88‌]

Me eee eeeeeeeeeeeeeeee ee eee-8-eee eeeeeeeee ee eeeeeeeeee(eeeeeeeeeeeeeee)eeeeeee(M) [Me(eeee)(MM)8] ee eee eeeeeeee ee e eeeeeeeee eeeeee ee ee eeeee eeeeee [8-eeeee-8-eeeeeeeeeeeeeeeee eee(eeeeeeeeeeeeeeeeeeeeeeee)eeeee], eee eeeeeeeee ee MMM eeeeeee ee eeeeeeee.[‌88‌] Meeeeee, eeeee eeeeeee eeeeeee eee ee eeeeee eeeeeeeee ee eeeee eeeeeee eee eeee eeee ee eeeeeeeee ee eee eeeee eee eeeeeeeeeee ee eeeeeeeeeeeeeeee. Me eeeeeeeeee, eeeeeee eee eeeeeeee ee ee eeeee eeeeee ee e eeeeeee, eee eeeeeeee ee eeeeeeeee eeeeee ee e eeeeeee–eeeeeeeee eeeeeeee.

Meeeeee—MMM eeeeeeeee ee eeeeeee eeee MeM(MMM)(eee), eeeeeee MMM eeeeeee eeeeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeee eeee eeeeeeeeee eeeee eeeeeeeeeeee ee eee eeeeeeee eeeee, eeee eeee eeeeee ee eee eeeeeeeeeeeeeeee ee eee-8-eee ee eeee eeeeeeeee 8 eee 8.[‌88‌] Meee eeee eeeeeee eee eeeeeeeeee eeeeee, eeeee eeeeeeeee ee eee eeeeeee eeeeeeeee ee eee-8-eee eeeee eee eeeeeee eeeeeeee eeeeeeeeee (88 °M, 88 eee). Meeeeee, ee eee eeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeee ee eeeeeeeee ee ee. 88% eee eee eeeeee/eeeeeeee eeeee eeeeeeee ee ee ee 8.8:8. Meeeeeeee eeeeeeeeee eeeeeeeee eeee eeee eeeeee; eeeeeee, eeee eee eeee(8M-eeeeeeee)eeeeeeeee eee eeee(8,8,8-eeeeeeeeeeeeee) eeeeeeeee ee eee eeeeee ee eeeeeeeee eeeeee 88%, eeee eeeeee/eeeeeeee eeeeee ee 8.8:8 eee 8.8:8, eeeeeeeeeeee. M eeeeee eeeee eee ee eeeeeeee eeeee eeeeeeee eeeeeeeee (88%); eeeeeee, eee eeeeee/eeeeeeee eeeee eeeeeeee ee eeee 8.8:8. Meeeeeeeeeeee eeeeeee eeee eeeeeeeee eee eeeeeeee ee eee eeeeeeeeeeeeee–MMM eeeeeeeeeeee 88 ee eee eeeeee eeee eeee(8,8,8-eeeeeeeeeeeeee) eeeeeeeee ee eeee, eeeeeeeeeeee eee eeeeeeeee ee eee eeeeeee—MMM eeee eeeee eee eeeeeeee eeeeeeeeee (Meeeee 88).[‌88‌] Me eeeeeeeeeee eeeeeeee [Me(eeee)(MMM)(MM), eeeee MMM = MMe, MMee] eeee eeeeeeee ee eeeeeeeee eeeeeeee ee eee eeeeeeeeeeeeeeee ee eee-8-eee ee eee eeeeeee ee e eeeeeeeeee eeeeee ee 88 °M eee 88 eee.[‌88‌] Mee eeeeeeeee eeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeee ee eeee(8,8-ee-eeee-eeeeeeeeeee) eeeeeeeee ee eeeeeee ee eeee eeeeeeee eeeee eeeeeeeeeeeeeee(eeeeeeeeee)eeeeeee [Me(eeee)(MM)8], eeeeeeeeeeee eee eeee ee eeeeeeeee ee eee MMM. Meeeeeeeeeeee ee eeeeeeeee eeeeeee eee eeeeeeeeeeeee eeee eee eee ee eee eeeeeeee eeee eee Me—MMM eeee ee eeeeeee ee eeee eeee.

Meeeee 88 Meeeeeeeeeeeeeee ee Mee-8-eee Meeee e Meeeeee—MMM Meeeeee eee Meeeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

Meeeeeee Meeee (8/8) Meeee (%) ee 8 eee 8 Mee
(MeM)8M 8.8:8 88 [‌88‌]
(8M-eeeeeeee)8M 8.8:8 >88 [‌88‌]
(M8MMM8M)8M 8.8:8 >88 [‌88‌]
(MeM)8M 8.8:8 88 [‌88‌]

Meeeeee eeeeeeeee 88 eee 88 eeeeeeeeeee ee MMM-88 eeee eeee eeeeee ee eee eeeeeeeeeeeeeeee ee eee-8-eee ee 888 °M eee 88 eee ee eeee eeeeeeeee 8 eee 88.[‌88‌] Meeeeeeee eee eeeeee eeee eeeeee ee 88–88% eeee eeeee eeeeeeeeee eeee eeeee eeeeee/eeeeeeee eeeeeeeeeee eeeeeeeee eeeeee eeeee eee eeeee eeeeeeeee eee eeeeee eeee 8.8:8 ee 8.8:8 eee eeeeeeee 88 eee eeee 8.88:8 ee 8.88:8 eee eeeeeeee 88. Me eeeeeee eeeeeeee ee eeeeeeee ee eeee eeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeeeeeeeeee ee Mee-8-eee Meeee ee MMM-88 Meeeeeeeeee Meeeeee Meeeeeee[‌88‌]

Meeeeeeeeee 88

Meeeeeee Meeeeeeee Meeee (8/88)e Mee
88 8.8–8.8:8 [‌88‌]
88 8.88–8.88:8 [‌88‌]

e Meeeeeeee eeee 8 eeeeeeeeee eeee.

Meeeeee—MMM eeeeeeeee eeee eeee eeee eeeeeeeeeeee eeeeeeeeeee ee ee eeeeeeeeeee eeeee-eeeeeee eeeee eeeeeeeee eee eeeeeeee ee eee eeeeeeeeeeeeeeee ee eee-8-eee eeeee 88 eee eeeeeeee ee eeee eeeeeeeee 8 eee 88 (Meeeee 88).[‌88‌] Me eeee eeeeeeeeeee eeee ee ee eeeeeee eee-eeeee eeeeee e eeeeeeee eeeeeeeee (MMM) ee ee ee 8888 e−8 ee eeeeeeee eeeee eee eeeeee/eeeeeeee eeeee eeeeeeeee eeee 88:88 ee 88:88. Me eee eeee eeeeeeee eeee, eeeee eeeeeeeeeeeeeeee eeeeeeeeee, eee eeeeeee eeeeeeeee 88 ee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeee eeeeeeeeeeeeee–eeeeeeee eeeeeee.

Meeeee 88 Meeeeeeeeeeeeeee ee Mee-8-eee Meeee e Meeeeee—MMM Meeeeee Meeeeeeeeee ee ee Meeeeeeeeee Meeee Meeeeeeee[‌88‌]

Meeeeeeeee eeeee eeeeeeeeeeeeee eeee MMM eeeeee eee eeee eeee eee eee eeeeeeeeeeeeeeee ee eeeeeee eeeeeeeee eeeeeeee eee eee eeeeeeeeeeeeeeee ee eee-8-eee eee eee-8-eee (Meeeee 88).[‌88‌] Me eeeee ee eeeeee eeeeee eeeeeeee eeee eeeee eeeeeeeee ee 88 eee eeeeeeee eeee eeeee eeee, ee ee eeeeeeeee ee eee e eee eeeeeee ee eeeeeeeee eeeeeeeee ee eeee eeeeeeee. Meee eeeeee/eeeeeeee eeeeeeeeeee, ee eeeeee 8:8, ee eeeeeeee eeee eeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeeee, eeeeeee eee eee ee eeeeeeeeeeeeeeeeee eeeee eeeee eeeeee/eeeeeeee eeeeee (ee. 8.8:8) eee eeeee eeeeeeeee.

Meeeee 88 Meeeeee—MMM Meeeeeeee Meeeeeeeeee ee Meeeeeeeeeeeee Meeeeeeeee Meeee eee Meeeeeeeeeeeeeee ee Mee-8-eee eee Mee-8-eee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee (8) eee 8-Meeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee ee Meeeeee-Meeeeeeeeeeeee MMM Meeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

Mee eeeeeeee eee eeeeeee eee ee e 88-eM eeeeeeeee eeee e eeeeeeeeee eeeeeee. Mee eeeeeeeee eee eeeeee ee e eee eeeeeee eeeeee eeeeeee e eeeee eeeeeee ee eeeeeeeeeee eee eeeeeeee ee eee eeeeeeeee. Mee eeee ee eeeeeeee 88 eee eeeeeeee eeeeeee e eeee ee eee eeee eee eeeeeeeee, eeeee eeee eee eeeeee eee eeeeeeeeeee ee 8–88 eee eeeee eee eeeeeeee eeeeeeee eee eeeeee ee eee eeeeeee eeeeeeeeeee. Mee eeeeeeeee, eee-8-eee, eee eeeeeeee eeee eee eeeeeeeee eeeee eeeeeeee eeee eee eeeeeee eeeeee. Meeeee eee eeeeeeee, eee eee eee ee eee eeeeeeeee eeee eee eeeeeee eeeeee ee eeee eee eeeeeeee eeeeeeee (88 eee). Meeee eee eeeeeeee eee eeeeee eeeee eee eeeeeeee ee MM.

8-Meeeeeeeeeeeee (88) eee 8-Meeeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee e Meeeeee Meeeeee Meeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

Mee eeeeeeee eee eeeeeee eee ee e eeeee-eeeee eeeeeeeee eeeee eee eeeeeee eeee eee eeeeeeee eeeeeeeee Me(MMe)(MMe)(MM)8, Me8M, eee eeeeeee ee eee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee eeeeeee (MMMMMMM: eeeeeeeeee), eee eee eeee eee eeeeeee eeeeeee. Mee eeeee eee eeeeee ee eee eeeeeeeee, eeeee eeeeeeeee ee eeeeeeeeee eeeeeee ee eeeeeee ee eeeeeee eeeeeeee eeeeeeee ee eee eeeee eeeee. Mee eeeeeeeee eee eeeeeee eeee eee eee eee eee eeeeee eee eeeeeeeeeee eeee MM eee M8. Mee eeeeeee eee eeeeeee ee eeeeeeeeeee ee eee eeeeeee eeeeeeee eeeeeeeeeee eee, eeeee eee eeeeeeee eee eeeeeeee, eee eeeeeeee ee eee eeeeeeeee eeee eeeeeeeeeee ee e eeeee-eeeeeeee eeeee eeeeeeeeee eeeeeeeeeeeeeeeee ee ee eeeeeeee eeeeeeee eee eee eeeee eee eeeeeeeee eeee eeeeee eeee MMMe8. Mee eeeee eee eeeeeeeeee ee 8M MMM eeeeeeeeeeee.

8-Meeeeeeeeeeeee (88) eee 8-Meeeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee e Meeeeeeee Meeeeee Meeeeeee Meeeeee e Mee(MMM) Meeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

Mee eeeeeeee eee eeeeeee eee ee e eeeeeeeee eeeeeeee eeeeeeeee eeee eeeeeeee eeeeeeee eee eeeeeeeeee eeeeeee. Mee eeee eee eeeeeeeee ee e eeeee eeeeee eee eee eeeeee eeee ee eee eeeee eee eeee eeee Meeeee. M eeee ee eee eeeeeeeee, eee eeeeeee eeeeeee 88, eee eee eeeeeee eeee eeeeee ee eee eeeeeeeee eeeeeeeee. Mee eee eeeeeee eee eeeeeeeeee, eee eeeeee eee eeeeee, eee eeeeeeee eee eeeeeeeee eeee eeeeeee eeeeeeeeeee eee eeeeeee. Mee eeeee eeeeeeee eeeeeee eee eeeeeee eee eeeeeeee ee MM. Me [eeeeeeeee]/[Me] = 888, eeeeeeeeeeee eeeeeeeeee ee eeeeeee eee eeeeeeee.

Meeeeeee (8) eee 8-Meeeeeeeeeeee (8); Meeeeee Meeeeeeee Meeee ee Me Meee Meeeee Meeeeeeeeeeeee—MMM Meeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

Meeeeeeee eeeeeeeee eeee eeeeeee eee ee eeee eee-8-eee ee e 88-eM eeeee eeeeeeeee eeeee eee eeeeeee eeee eee eeeeeeee eeeeeeeee eee eee eeeeeeeeee eeeeeeee eeeee e M8 eeeeeeeeee. Meee, eee eeeeeeeee eee eeeeee eeee ee eeeeeeeee eeeeeee ee M8 eee MM ee 88 eee eee eeeeee ee 88 °M eeee eeeeeeee eeeeeeee. Meee eee eeeeeeee eee eeeeeeee, eee eeeeeee eeeeeeee eeee eeeeeeeee eeee eee eeeeeeee ee eeeeee eeeeeeee eee eeeeeeee ee MM.

Meeeeee (8) eee 8-Meeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee ee MMM-88 Meeeeeeeeee Meeeeee Meeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

Meeeeeeee eeee eeeeeee eee ee ee eeeeeeeee eeeeeeee eeee e eeeee eeeee eee e eeeeeeee eeeeeee. Mee eeeee eee eeeeeee eeee eee eeeeeeeeeee eeeeeeee, eee-8-eee, eee eee eeeeeee. Mee eeeee eeeee eee eeee eeeeeee eeeeeeee eee eee eeeeeeee eeeeeee eee eeeeeee eeee M8/MM. Mee eeeeeeeee eee eeeeeeeeeee ee 88 eee, eeeeee ee 888 °M, eee eeeeeee eee 88 e. Meeee eeeeeee, eee eeeeeeee eeee eeeeeeee eeeeeee e eeeeeeeeeeeee eeeeeeee eee eee eeeeeeeee eeeee eee eeeeee eeee eeeeeee. Mee eeeee eeeeeeee eee eeee eee eee eeee eeeeeeeee eeeee eee eee eeeeeeee eee eeeeeeee ee MM.

Meeeeee (8) eee 8-Meeeeeeeeeeee (88); Meeeeee Meeeeeeee Meeee ee Meeeeeeeeee Meeee Meeeeeeee Meeeeeeeeee Meeeeee Meeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

Mee eeeeeeeee eeee eeeeeee eee ee e 888-eM Meee eeeeeee. Mee eeeeeee eee eeeeee eeee eeeeeee eeeeeee eeeeee ee eee eeeeeeeeeee, eeeeeeeee M8M, eee eee-8-eee eee eeee eeeeeee eee eeeeeeeeeee eeeee eeee MM/M8 (8:8; 88 eee). Mee eeeeeeeee eee eeee eeeeee ee 888 °M eee eeee ee eeee eeeeeeeeeee eee 8 e. Meeee eeeee eeeeeeeeee, eee eeeeeee eeeee eee eeeeeeee ee MM.

References