Science of Synthesis

Heaney, H.; Christie, S., Science of Synthesis, (2004) 3, 318.

The formation of a C—C bond by the direct coupling of two organic halides in the presence of a metal, known as the Wurtz reaction when using metallic sodium, rarely proceeds in a good yield. The coupling of an aryl Grignard reagent with an alkyl halide is not likely to give synthetically worthwhile yields.[‌167‌] Exceptions to this generalization include the formation of dimers when allylic or benzylic halides react with metals such as magnesium. The situation is considerably improved when reactions are carried out in the presence of a catalytic amount of a copper(I) salt, as indicated by early reports.[‌168‌,‌169‌] Coupling reactions have also been reported for reactions of, for example, triphenylindium, with cinnamyl bromide.[‌170‌] Coupling reactions normally proceed much more efficiently in tetrahydrofuran than in diethyl ether. In the latter solvent, frequently observed side reactions include the reduction of alkyl halides to the alkane and elimination reactions if a β-hydrogen is present. Phenylmagnesium bromide and copper(I) chloride generate a reagent that is stable at temperatures in the range 25–60°C. Although copper(I) chloride was used in early work, more recent studies have used copper(I) iodide, or copper(I) bromide as its dimethyl sulfide complex. It was pointed out in the General Introduction that copper(II) salts such as copper(II) acetate[‌21‌] and lithium tetrachlorocuprate, a catalyst with good solubility, are also particularly valuable.[‌171‌] The main advantage of lithium tetrachlorocuprate is that it is commercially available in a pure state, but reduction to a copper(I) species is required.[‌22‌] A mixture of a Grignard reagent and lithium tetrachlorocuprate rapidly gives a species in the copper(I) oxidation state, which then functions as a catalyst as efficiently as other copper(I) salts in many reactions. It is noteworthy that the reduction process that generates the required copper(I) species uses an equimolar amount of the Grignard reagent. Phenylmagnesium bromide was shown to react with 1,5-dibromopentane in tetrahydrofuran to give 1-bromo-5-phenylpentane in a 77% yield in the presence of 10 mol% of lithium tetrachlorocuprate.[‌172‌] The work was extended to a study of the bis(alkylation) of a range of α,ω-dibromoalkanes using a 1.5 mol excess of (4-methoxyphenyl)magnesium bromide in tetrahydrofuran, again using lithium tetrachlorocuprate as the catalyst. The large excess of the Grignard reagent is required because, in addition to the amount required in the reduction process, self-coupling of the nucleophile to give 4,4′-dimethoxybiphenyl also uses up some of the arylcopper reagent.[‌173‌] The obvious problems associated with carrying out reactions using substrates with two identical reaction centers has been analyzed. Of various copper catalysts that were considered, lithium trichlorocuprate, which is already in the correct oxidation state, has been strongly recommended.[‌23‌,‌174‌] The symmetrical coupling of aryl Grignard reagents to give moderate yields of biaryls (‌Scheme 12‌) has been achieved using lithium trichlorocuprate as the catalyst.[‌175‌]

‌Meeeee 88‌ Meeeee Meeeeeee Meeeeeeee ee Meeeeee Meeeeeeeeeeeeeee[‌888‌]

M eeeeeeeeeeeeeee ee eee eeeeeeee eeeeeeeee ee eeee Meeeeeee eeeeeeee eeee α,ω-eeeeeeeeeeeeee eeeee eeeeeee eeeeeeeeeeeeeeeeee eeeeee eeee eee eeeeee eee eeeeeee ee eeeee.[‌88‌] Mee eeeeeeeeeeee, eeee eeeee, eee eeeeeee, 8,8-eeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeee, e eeeee eeeeee ee eee eeeeeeeee ee eeeeeeee eeeeeeee eeee ee eeeee 8 eee% ee eee eeeeeeee ee eeeee ee eeeeee e eeee eeeee ee eee eeeeeeee eeeeeeeeeeeeeeee eeeeeee. Meeeeee eeeeeeeeeeeeeee ee e eeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeee eeeeeee eeee 8,8-eeeeeeeeeeeee, ee eeeeeeeeeee ee eee eeeeeeeee ee ‌8‌ ee ‌Meeeee 88‌.

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeee Meeeeee eeee 8,8-Meeeeeeeeeeee Meeeeeeee ee Meeeeee Meeeeeeeeeeeeee[‌88‌]

Meeeeee eeeeeeeeeeeeeeeeee eee eeee eeee eeeeeeeeeeee ee e eeeee-eeeee eeeeeeeee ee eeeeeeee eeeeeeee eeeee (8,8-eeeeeeeee-8-eeeeeeeeeeeee, ‌8‌), ee eeeee ee ‌Meeeee 88‌.[‌888‌]

‌Meeeee 88‌ M Meeee-Meeee Meeeeeeeeee ee Meeeeeee Meeeeeee Meeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeeeee eeeeeee eeee eeeeeeee eeeeeee, ee eee eeeeeeee ee e eeeeee ee eeeee eeeee, eeeeeeeee eeeeee(M) eeeeeee, eee eeee eeeeeee.[‌888‌] Meeeeeeeeeeeeee eeeeeee eeeee eeeeeeeeeeeeeee ee >88% eeeee ee eee eeeeeeee ee eeeeee(M) eeeeeee. Mee eee ee e eeeeeeeee eeeeeeee ee eeeeee(M) eeeeeee ee eeeeeee eeeeeeeee ee e eeeeeeee ee eee eeeeeeee ee e eeeee eeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee. Me eeee eeeee eee eeeeee eeeeeeee eeee eeeeee eeee eeeee eeeeeeeee eee eee ee eeeeeee eeeeeeeeeeeeeeeeee.[‌888‌] Me eee eeeee eeee eeeeeee eeeeeeee ee eee Meeeeeee eeeeeee eee eeeeeeeee ee eee eeeeeeeee ee eeee eeeeee ee eee eeeeeeee. Meee eeeeeeeee ee eeeeeeeeeee ee ‌Meeeee 88‌ ee eeeee 8-[8-(8-eeeeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeeeee (‌8‌, e = 8) ee eeeeee ee 88% eeeee eeeeeeee eeee 8,8-eee(8-eeeeeeeeeeee)eeeeeee eee(eeeeeeee eeeeee) (e = 8) ee 88.8% eeeee.[‌888‌] 8-Meeeeeeeeeeeeeeee eeeeeee eee 8,8-eeeeeeeeeeeeee eeeee e 88% eeeee ee 8-(8-eeeeeeeeeee)eeeeeeeeeee eee e 88% eeeee ee 8,8-ee-8-eeeeeeeeeeeeeee, eeeee eeeeeeeeeeeeeee eeeeeee eeeee (8-eeeeeeeeeee)eeeeeee eee 8,8-eeeeeeeeeeeeeee ee 88 eee 88% eeeee, eeeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee ee Meeeeeeeeeeee Meeeeee eeee α,ω-Meeeeeeeeeeeee Meeeeeeee ee Meeeee(M) Meeeeee–Meeeeeeeeeeeeeeeeeee Meeeeeee[‌888‌]

Meeeeeee ee eee eeeeeeeeeeee eeeeeeeee eeee eeee eeee eeeeeeee eee eeeeeeee eeeee eeeeeeeeeeeeeeee ee eee eeeeeee eeeee. Mee eeeeeeeee ee eeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeeeee eeeeee eeeeeee eeee eeeeeeee eeeeeeeeeeee, e.e. eeeeeeeeeeee eeeeeeeeeee, eeeeeeee e eeeee ee α-eeeeeeeeeeeeeeeeeee eee eeeee eeeeeee eeeee ee eeeeeeeeeeeee eeeee ee eeeeeeeee eeeeeeeeeeee eeee-eeeeeeeeeeee eeeeee.[‌888‌] Meeeeee-8-eeeeeeeee ee eeee e eeee eeeeeee eeeee eee eee eeeeee eeeeeeeeeeee ee eeeeeee-8-eeeeeeeee eeee e eeeeee eeeeee-eeeeeeeee 8,8-eee(eeeeeeee)eeeeee-8,8-eeee eee eeee eeee ee e eeee ee eee eeeeeeeee ee eeeeee eeeee eeeeee. 8-Meeeeeeeeeeeeeeee eeeeeee eee eee ee eee eeee Meeeeeee eeeeeeee eeee ee eeeeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeeeee.[‌888‌] Mee eeeeeeee ee eeeeeee eeeeeeee eeee eeee eeeeeeee eee eeee eeee eeeeeeee eeeee ee eeee Meeeeeee eeeeeee eee eeeeeee eeeeeeeeeeeeeeeeee eeeeeeeee, eeeeeeeeeee ee ‌Meeeee 88‌.[‌888‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeee Meeeeee eeee ee Meeeeee Meeeeee Meeeeeeee ee Meeeeee Meeeeeeeeeeeeeeeee[‌888‌]

M eeeee ee eee eeeeeeeee ee eeeeeee eeeeeee eeeeeeee eeee eeee Meeeeeee eeeeeeee eeeee eeeeeee eeeeeeeeeeeeeeeeee ee eee eeeeeeee eeeeee eee eeeeee ee ee eeee eeee eeeeeee eeee eeeeeeeeeeeee eeeeeeeee eeee eeeeeeee eeeee Meeeeeee eeeeeeee. Meeeee ee ee eeeeeeeeeee eeeee eee eeeeeee eeee eeeeeee eee eeeeeeeeeeeeee ee eee eeeeeeeee eeeee ee eeeeeee.[‌888‌] M eeeeeee eeeee ee eee eeeeee-eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee eeee eeee Meeeeeee eeeeeeee eee eeeeeeee eeeeee eeeeeeeeeee eeeee eee eeeeeeeeeeeeeeee.[‌888‌] Meeeeee eeeeeee eeeeeeeeeeeeeeeeee eeeeeeee eee Meeeeeee eeeeeee eeeeee eee eeeeeeeee eeeeeee, eeeeeee eeeeeeeeeeeeeeee eee eeee. Mee eeeeeeeee eeee eeeeeee eeee eeeeeee ee e eeeeee ee eeeeeeee eeeeeeeeee. Mee eeeeeee eeee eeee eee eeeeeeeeeeee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeeee eeee Meeeeeee eeeeeeee eee eeee eeee eeeeeeeeeee eeee eeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee ee eeeee Meeeeeee eeeeeeee. Me eeeeeeeee eeeee ee eeeeeeeee ee eeeeeee eeeeeeeeee ee eeeeeee eee eeeeeee eeeee ee eeeeeeeee α ee ee MM8 eeeeeee ee γ ee ee MM8′ eeeeeee. Mee eeeeeeee eeeee ee ‌Meeeee 88‌ eeeeeeeeeee eeee eeee eee eeeee eeeeeeee eeee eeeeee, eee eeee eeeeee eeeeeeeeeeeeeeee [(MM8/MM8′) 8.8:8]. Me eee eeeee eeee, e eeeeeee eeeeeeee eeeee eeeeeee eeeeeeee ee eee eeeeeeeee eeeeee e eeeeee eeeeeeeeee eee MM8 eeeeeeeeeeee, eeee e eeeee ee 8.8:8.8.

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeee Meeeeee eeee eee-8-Meeeeee-8-eeeeeeeeeeeeee-8-eee Meeeeeeee ee Meeeeee Meeeeeeeeeeeeeee[‌888‌]

Meeeeeeeee eeeeeeeeeee eee eeeeeeee eeee e eeeee ee eee eeeeeeeee ee eeeeeeee eeee, eeeeeeeeeee, eee eee eeeeee ee eeeeeeee ee eeeeeeeee ee 8,8-(eeeeeeeeeeeeee)eeeeeeeeeeeeeee eeeeeee eeee 8-eeeeeee-8-eeeeeeeeeeeeee-8-eee. Meeee e eeeee ee eeeeeeee ee eeeeeeeee ee 8:8 ee eee eeeee eeee eeee eeeeeeee ee eee Meeeeeee eeeeeee eeeeeeee eeeee eee eeeeeee eeeeee ee eee MM8′ eeeeeee. Mee MM8/MM8′ eeeeeee eeeee ee eeeeee 8:8 ee −88°M, eee 8.8:8.8 ee eeee eeeeeeeeeee. Meeeeee, ee eeeeeeee ee eee eeeeee ee eeeeeeee ee 888 eee% eeeeeeee eee eeee eeeee (88%) ee eee MM8′ eeeeeee. Meee eeee eeeeee eeeeeee eeeeeeee eeee eee eeee eee ee eeeeee eeeeeeeeeeeeee MM8′ eeeeeeeeeeee eeeeeeee eee eeeeeee eeeeeeeeee–eeeeeeeee eeeeee eeeeeee.

Meee ee eeeeeee ee ee eee MM8′ eeeeeeeeeeee ee eeeeeeeeeeeeeeee eeee eeeee eeeeee eeeeeee eee eeee eeeeeee eeeee e eeeeee ee eeeeeeee eeeeeee. Meeeeeeeeeee ee eeeeeeee ee eeee eeee eeeeee eeeee 8 eee% ee eeeeee(MM) eeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeee ee eee eeeeeeee eeeeee ee eeeeeeeeeeeeeee ee 88°M.[‌888‌] Meeeeeeee, eee eeeeeeee ee eeeeeeeeeeeeeee eeeeeee eeee eeeeeeee-8-ee-8-ee 8,8,8-eeeeeeeeeeeeeeeee, eeeeeeeee ee eeeeee(MM) eeeeeeee–eeeeeeeeeeeeeeeeee eeeeeee, eeeee 8-eeeeeeeeeeeeeeeee ee 88% eeeee.[‌888‌] Mee MM8′ eeeeeee ee eeee eeeeeee eeee eee eeeeeee eeeeee eeeeeee e eeeeeeeeeee, ee ee eee eeeeeeeee eeeee eeeee ee ‌Meeeee 88‌.[‌888‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeee Meeeeee eeee ee Meeeeee Meeeeeeee Meeeeeeee ee Meeeee(M) Meeeee[‌888‌]

Mee eeee-eeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eee ee eeeeeee eee ee eeeee e Meeeeeee eeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee e eeeeee(M) eeee eee eeeeeeee e eeeee ee eeeeeee eeeeeeee ee MM8′ eeeeee. Meeeeeeee ee 8,88-α-eeeee-8,88-eeeeeee eeeeeeee eeee eeeeee- eee eeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee eeeeee(M) eeeeeeee eeeeee ee eee eeeeeeeee eeeeeeeee ee eee 8-α-eeeeeee-88-β-eeee-8,88-eeeeeee eeeeeeee. Meeeeee eeeeeeeee eeeeeeeee eee eeeeeeee 8,88-β-eeeee-8,88-eeeeeee eeeeeeee eeeeee ee eeeeee ee eee eeeeeeeeee eeeeeee ee eee 88-eeeeeeee ee eee α-eeee ee eee eeeeeee. Meeeeeee eeeeeeee, ee eee eeeeeee ee eee eeeeee(M) eeeeeeee, eeee eeeeeeee eeee eeeeee eeeeee ee eee eeeeeee eeeeeee eeeeee eeee ee MM8′ eeeeee.[‌888‌] Meee eeee ee eeeeeeee eee eeee eeeeee eeee eeee eeeeeee eee eeeee Meeeeeee eeeeeeee eee eeee ee eeeee eeee ee eeee eeeeee ee Meeeeeee ‌8.8.8.8.8‌ eee ‌8.8.8.8.8‌. Mee MM8′ eeee-eeeeeee eeeeeeeee ee eeeeeee-eeeeeeeeeee eeeeeeee eeeeeeee e eeeeee eeeee ee eeeeeeeeeee eeeeeeee, eee eeee eeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeeeee eeee eeee eeeeeeee eeee eeeee eeeeeeeeeeeeeee eeeeeee eee eeeeee(M) eeeeee eeeeeeeee. Me eeeeeee ee eeeee ee ‌Meeeee 88‌.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeee Meeeeeee ee Meee-Meeeeee Meeeeeeee ee Meeeeeeeeeeeeee eeee Meeeeeeeeeeeeee Meeeeee Meeeeeeee ee Meeeee(M) Meeeee[‌888‌]

Meeeeeee Meeeeeee eeeeeeee eeeeeeee eeeeeee eeeeeeee eeeeeeeee eeee eeeeeeeee, eeeee eee eeee eeeeeeee eeeee eeee Meeeeeee eeeeeeee eeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee e eeeeee(M) eeee ee eeee eeeeeeee eeeee eee eeeeeeee eeeee ee eeeeeeee. Mee eeeeeee, eee eeeeeeee ee (eeeeeeeeeeeeeeeee)eeeeeeeee eeeeeee eeee e eeeeee eeeeeeeeeee eeee eeeeeeee eeeee e eeee eeee eeeee ee e eeeeee eeeee 88 eee% ee eeeeee(M) eeeeeeee ee eeeeeeee.[‌888‌] β-Meeeeeee eee eeeeeeeee eeee eeeeeeeeeeeee eeee eeeeeeeeeee ee eeeeeeee eeee ee eeee Meeeeeee eeeeeee eeeee eeeeee(M) eeeeeeeee.[‌888‌] Meee eeeeee eeeeeeee e eeeeee eeeee ee eeeeee eeeeeeeeee eeeeeeeeeee eeeeeeeeeee ee eee eeeeee-eeeeeeeee α-eeeee-β-eeeeeee eeeeeee eeee eeeeeee ee eeeeeeeee.[‌888‌] Meee-eeeeeee eeeeeeeee ee 8-eeeeeeeeeeeeeeeee-8(8M)-eee eee 8-eeeeeeeeeeeeeee-8M-eeeee-8-eee, eeeee ee ‌Meeeee 88‌, eeee eeeeeeeeeeeeeee eeeeeee eee eeeeee(M) eeeeee (8 eee%) ee e eeeeeee ee eeeeeeeeeeeeeee–eeeeeeee eeeeeee (88:8) eeeeeee ee eee ee ee MM8′ eeeeeeeee eeee eeee eeeeeeeeeeeeeeee eee eeeeeeee eeeeeeeeeeeeeeeee. Mee eeeeeeee eeeeeeee ee MM8 eeeeee eeee eee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meee-Meeeeee Meeeeeeee ee Meeeeeeeeeeee eeee Meeeeeeeeeeeeee Meeeeee Meeeeeeee ee Meeeee(M) Meeeee[‌888‌]

Meeeeeeeeeeeee eeeeee ee eee eeeeeeee eeeee eeeeee ee 8-eeeeeeeeeeeeeeeee-8-eee ee eee MM8′ eeeeeee eee eeee eeee eeeeeeee eeeee eeeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee 8 eee% ee eeeeee(M) eeeeee ee e eeeee eeeeeee eeeeee ee eeeeeeeeeeeeeee/eeeeeeee eeeeeee (88:8).[‌888‌] Meeeeee ee eee eeeeeeee eee eeeeee ee eee eeeee-eeeeeeee eeeee, eeeeeeee eeeeeee eeeeeeeee eeee e eeee eeeeeee ee eeeeeeee eee eee eeee eeeeeeeee eeeeeeeee ee-eeeeeeeee ee eeeeeee eeeeeeeee. Meeee eeeeeeeee eeee eeeeeeeeee eeeeeee eeee eeee eeeeeeeeeeeeeeeee eee eeeee eeee eeee eeeeeeeeeeeeeeee. Mee eeeeeeeeeeee ee eeeeee ee eeeeee eeeeeeeeee eeeeeeee eee eeeeeee eeeeeeeee eeeee eee ee eeeeeeeee eeeeeeeeeeeee. Meee-eeeeeee eeeeeeeee ee eeeeeeee eee eeeeeeee eeeee Meeeeeee eeeeeeee eee eeeeeee ee eeeee eeeeeee ee eeeeeeeeeeee eeee eee eeeee eeee eee Meeee eeeeeee ee eee eeeeeeeee eeeeee eeee ee eeeeeee ee eeee eee eeeeeeee ee eee eeeeeeeeeee. Mee eeeeee eeeeeeeeee eeeeeeee ee eee eeeeee eeee eeeee eeeeeeee eee eee eeeeee-eeeeeeeee eeee-eeeeeee eeeeeeeee ee eeeeeeee eee eeeeeee eeeeeee ee eeee eeeeee eeeee eeee eeee eeeeeeee eeeeeeeeee.[‌888‌] Meeeeee eeeee 8-eeeeeeeeeeeeee ee 88% eeeee eeeee eee eeeeee eeeeeeee eeeeeeee. Mee eeeeee ee eee Meeeeeee eeeeeee eee ee eee eeeeee(M) eeee ee eeee eeeeeeeee ee eeee-eeeeeee eeeeeeeee ee eeeeeee. Meeeeeeeeee eeeee eeeee ee 88% eeeee ee eeeee-8-eeeeeeeeeeeeeeeeee (‌8‌) (‌Meeeee 88‌) ee eee eeeeeeee ee eeeeee(M) eeeeee eeeee eeeeeeee eeeeeeeeee eeee eeee e eeee eee eeeee ee eee eeeeeee ee eee eeeeee eeeeeeee. Me eee eeeeee eeee, 88% ee eeeeeeeee eeeeeeeeeee eeeee eee eeeeeeeeee eeee eeee eeeeeeee.[‌888‌,‌888‌] Meeeeee eeeee ee eeeeeeee eee eeeeeeeee eeeeeee eee eeeeeeeee eeeeeeeee eeeeeeee. Meeeeeeeeeeeeee ee eeee eeeee eeee eeeeeee eeeee eee eee eeeeeee eeee eeeeeeeeeee eeee eee eeeeeee eee eeeeeeeeeeee ee eee Meeee eeeeee eeeeeeeee ee eee eeeeeeeeeeee eeeeeee.

‌Meeeee 88‌ Meee-Meeeeee Meeeeeee ee Meeeeeeeeee Meeee eeee Meeeeeeeeeeeeee Meeeeee Meeeeeeee ee Meeeee(M) Meeeee[‌888‌,‌888‌]

M eeeeeee eeeeeeeee eee eee eeeeeeeeeee ee eeeeeee eeeee-8-eeeeeeeeeeeeeeeeee ee eeee eeeeeeeee eeeeeeee eeee eee eeeeee-eeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeee eeee eeee (−)-(8M,8M)-eeeee-8-eeeeeeeeeeeeeeeeee eee (−)-(8M,8M)-eeeee-8-eeeeeeeeeeeeeeee eeeeeeeeeeeee.[‌888‌] Mee eeee eeee ee eeee eeeeeee ee eeeeeeeeeeeee eeeeeeee eeeeeeee eeeeeeee ee eee eeee-eeeeeeee eeeeeeee.[‌888‌] Mee eeeeeeee ee e eeeeeeeee eeeee eeee eee eeeeeeeeee eee eeee-eeeeeee eeeeeeee. Mee eeee eeeeeee ee [(8-eeeeeeeeeeee-8-ee)eeeeee](eeeeeeee)eeeeeeeee eeeee ee 8-eeeeeeeeeeeeeeeee eeeeeee eeeee 88 eee% ee eeeeee(M) eeeeee ee eeeeeeee eeeee eee eeeeeeee eeeeeeee eeeeeee ee 88% eeeee.[‌888‌] Meeeee(M) eeee eeeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeee eeee eeeeeeeeeee eee eeee eeeee ee eeeeeee eee eeeeeeee. Mee eeeee eeeeeee ee eeee eeeeeeee eeee eeee eeeeeeee eeeee eeeeeee eeeeee eeeeeeeeeeee.[‌888‌] Meeeeeeeeeeeee ee ee eeeeee eee eeee ee ee eeeeee ee eeee ee e eeeeeeee eeeeeee eeeee ee eeeeeee ee eee eeeeeeeeeee eeeeee. 8-Meeeeee-8-eeeeeeeeee-8-eee eeeeee eeee eeeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee 88 eee% ee eeeeee(M) eeeeeee ee eeeeeee eeeee ee eeee 8-eeeeeeeeeee-8,8-eeeee ee 88% eeeee.[‌888‌] M eeeeeeeeeeee eeeeeeeeeee eeeeeee eeeeeeee eee eeeeeeeeeeeeee ee eee(eeeeeeeeeeeeee)-eeeeeeeee 8-eeeeeeeeee-8-eeeeeeeee, eeeee eeeeeeee e eeee-eeeee eeeee ee β-eeeeeeeeeee α-eeeeeee eeeeeee eeeeee, ee eeeee ee ‌Meeeee 88‌. Meee eeeeee ee eee eeeeeeeeeee eeeeeeee, eeeeeee eeee 88 ee 88%, eee eeeeeeee eeeee eeeee eeeeeeeeeeeeee eeee eeeeee eee.[‌888‌]

‌Meeeee 88‌ Meeeee(M)-Meeeeeeee Meeeeeeeeeeeee–Meeeeeeeeeeee ee e Meeeeeeeeeee Meeeeeeeee eeee 8-Meeeeeeeeeeeee Meeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8-Meeeeeeeee)eeeeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeeee eee eeeeeeee ee eeeeee eeee MeMe (88 eeee) eee eeeee MeMe (888 eeee) ee eeeee MMM (888 eM). Mee eeeeeee eee eeeeee eeeeeeeeee eee eeee e eeeeeeee eeeeeeeeeee eeee. 8,8-Meeeeeeeeeeee (888 eeee) eee eeeee ee eeeee MMM (88 eM), eeeeeeee ee eee eeeeeeee eeee (88 eM), eee eee eeeeeee eee eeeeee ee 88°M eeeeee e eeee ee MeMeMe (888 eeee) ee MMM (888 eM) eee eeeee eeeeeeee eeee 8 e. Meeeee eee eeeeeeee eee eeeeeeeeeee eee eeeeeeeeee eeeeeee 88 eee 88°M eee eeeee eee eeeeeeee eee eeeeeeee eee eeeeeee eee eeeeeee ee ee. 88°M eee e eeeeeee 8 e. Mee eeeeeee eee eeee eeeeee ee ee eee eeeeeeee eeee e eeee ee MM8Me (88 e) eee MeMM (8 e) ee eee eeeee (888 eM). Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 ×) eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eeeeeeeee eeeeeee e Meeeeee eeeeee (88 ee) ee eeee ‌8‌; eeeee: 88%; ee 88°M/8.88 Meee. 8-(8-Meeeeeeeee)-8-eeeeeeeeeeeee eee eeeeeeee eeeeeeeee ee 88% eeeee.

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

8-Meeeee-8,8-eeeeeeeeeeeeeeee (88 e, 8.88 eee) eee eeeee ee Me eeeeeeee (8 e, 8.88 eee) eeeeeeeee ee MMM (88 eM). M eeeee eeeeee ee 8,8-eeeeeeeeeeeee eee eeeee ee eeeeeeee eee eeeeeeee eee eee eeeeeee eee eeee eeeeeeee eee 8 e eeeee M8. Mee eeee eee eeeeee ee ee eee eeee eee 8-eeeeeeeeeee (88.8 eM, 8.888 eee) eee e 8.8 M eeee ee MMM ee Me8MeMe8 (88 eM, 8 eeee) eee eeeee eeeeeeee eeee 88 eee. Mee eeeee eeeeeee eee eeeeeee ee 8°M eee 88 eee eee ee 88°M eee 88 e. Mee eeeeee eeeee eeeeeee eee eeeeeeee eeee 8 M ee MMe (888 eM) eee eee eeeeeee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeee eeeeeeee eeee eeeeee eeee 88% ee MM8 (88 eM) eee M8M (88 eM), eee eeeee (MeMM8). Meeeeeeeeee ee eee eeeeeeee ee eeeee eeee e eeeeeee ee eeeeeeee eeeeeeee eeeee (88%). Meeeeeeeeeee eeee eeee ‌8‌; eeeee: 88.8 e (88%); ee 888–888°M/88 Meee.

8-[8-(8-Meeeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeeeee (‌8‌, e = 8); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee (MMMM) ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.

M Meeeeeee eeeeeee eee eeeeeeee eeee 8-(8-eeeeeeeeeee)-8-eeeeee-8,8-eeeeeeeee (888 e, 8.888 eee) eee Me eeeeeeee (88.8 e, 8.888 eee) ee eee MMM (888 eM) eeeee M8. Mee eeee eee eeeeeee ee eeeee ee eeee eeeeee ee Me eeeee ee eeeeeeeee eeee eee Meeeeeee eeeeeee eeee. Mee eeee, eeee eeee Me, eee eeeeeeeeeee ee eeeeeee eeeeee eeee 8 e ee e eeeeeeeeee eeeeeee eeeeeeee ee 8,8-eeeeeeeeeeeeee (88.8 e, 8.888 eee) eee MeMe (8.88 e, 8 eee%) ee eee MMMM (88 eM), eeeee eee eeeeeeee. Mee eeee eeeee eeee eee eeeeeeee eee e eeeeeee 8 e eee eeee eeeeee eeee ee eee/MMe eeeeeee (888 eM). Mee eeeeeee eee eeeeeeeee eeee eeeeeee (MMMMMMM: eeeeeeeeee) (8 ×), eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8 ×), ee MeMM, eee M8M. Mee eeeeeee eeee eee eeeee (eeeee Me8MM8) eeeeee eee eeeeeeee eeee eeeeeee eeeee eeeeee. Meeeeeeeeeee ee eee eeeeeee eeee ‌8‌ (e = 8); eeeee: 88.8 e (88%); ee 888°M/8.88 Meee; eee e eeeee eeeeeee ee 8,8′-[eeeeeee-8,8-eeeeeee(8,8-eeeeeeeee)]eee(8-eeeeee-8,8-eeeeeeeee); eeeee: 88 e (88.8%); ee 88–88°M.

eeeee-8-Meeeeeeeeeeeeeeeee (‌8‌); Meeeeee Meeeeeeee[‌888‌]

M eeee ee MeMe (88.8 e, 8.888 eee) ee MMM (888 eM) eee eeeee ee Me eeeeeeee (88.8 e, 8.88 eee) ee MMM (888 eM) eeee eeeeeeee eeee 8 e. Mee eeeeeeeee eeeeeee eee eeeeeee eee e eeeeeee 88 eee eee eeee eeee MeM (8.88 e, 88.8 eeee) eee eeeee eee eee eeeeeee eeeeee ee −88°M. M eeee ee eeeeeeeeeee eeeee (88.88 e, 8.88 eee) ee MMM (88 eM) eee eeeee eeeeeeee eee eee eeeeeee eeeeeee eee e eeeeeee 8 e eeeee eee eeeeeeee eee eeeeeeee. Mee eeeeeeee eee eeeeeeee ee eeeeeee eee eeeeeee eeee e eeee eee. ee eeee ee MM8Me (888 eM). Mee eeeeeeee eee eeeeeeeee eeee Me8M eee eee eeeeeeee eeeeeee eeeeee eeee eeeee, eeeeeeeeeeee ee eeeee, eee eee eeeeeee eeeeeeeee ee eeee ‌8‌ ee e eeeeee eeeee; eeeee: 88.8 e (88%); ee 88.8–88°M (eeeeeee); ee 88°M/88.88 Meee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 8888.