Navigation

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
3.4.4.1.1 Variation 1: Substitution Reactions Using a Catalytic Amount of Copper Salt

DOI: 10.1055/sos-SD-003-00274

Heaney, H.; Christie, S.Science of Synthesis, (20043529.

There are a wide range of reactions documented using Grignard reagents with catalytic quantities of copper salts. Many of these have been collected in tabulated form in other published reviews of the area. In particular, Lipshutz's monograph has provided an excellent central source of knowledge up to the early 1990s.[‌3‌] This section will attempt to bring these data together with more recent examples, and to generalize as to the applicability of certain reactions and conditions in commonly encountered reaction types. The use of only catalytic quantities of copper often imparts different selectivity and reactivity to the intermediate organometallic reagent. In general, the addition of a copper source allows coupling reactions of alkyl halides and Grignard reagents to take place in good to high yield, whereas without the copper the reaction often takes a different course. In addition, this allows substrates and functionalities that would not normally be tolerated by a Grignard reagent to be utilized. In the examples in Scheme 300, ester groups are tolerated by the Grignard when used in the presence of catalytic quantities of copper salts.[‌1352‌,‌1353‌] Other examples have used phosphates as additives during similar coupling reactions.[‌1354‌]

Meeeee 888 Meeeeeeeeeee ee Meeeeee Meeeeee Meeeee eeee Meeeeeee Meeeeeee eee e Meeeeeeee Meeeeeee ee Meeeee Meee[‌8888‌,‌8888‌]

Meee ee eeeeee eeeeeee eee eeeeeee ee eee eeeeeeeee, eeeee eee ee eeeeeeeee ee eeeee eeeeeeeeeee eeeeee ee eeeeeeeeeeeee ee eee Meeeeeee eeeeeee eeeeee eee eeeeeeee eeee eee eeeeee eeeeee ee eeee. Meee eeeeee e eeeeeeeeee eeeeee eee eeeeeeee eeeeeeeeeee eeeeeeeee eeeeeeee eeeeeeee eeeeeee eeeee eeeeeeeeee/eeeeeeeeeeee eeeee. Me eee eeeeeeee eeeee ee Meeeee 888, eeeeeeeeeeeee ee eee eeeeeeeeee eeeee eeeeeee ee eee eeeeeeeee eeee eee eeeeeeeee eeee eee eeeeeeeeeeee ee eee eeeeeee. Mee eee eeeee ee eee eeeee eeeeeee ee eeeeeeeeeee ee eee eeeeeeeee ee eeee Meeee eeeeeeee eeeeeeee; eeeeeee, eee eeeeeee eee eeeeeee ee eeee eee eeeeeeeeeee eeee, eee eeeeeee eee eeeeee eeeeeeee.[‌8888‌,‌8888‌]

Meeeee 888 Meeeeeeeeeee ee Meeeeee Meeeeee Meeeee eeee Meeeeeee Meeeeeee eee e Meeeeeeee Meeeeeee ee Meeeee Meee[‌8888‌]

Me e eeeeeee eeeeee, eeeeeeeee eee ee eeeeeeeee ee eeee eeee eee eeeeeeeeeeeee eeeeeee, eeeeeeeeeeeee eee eeeeeeeeee ee eee eeeeee eeeeeee eeeee (Meeeee 888).[‌8888‌,‌8888‌] Meeeeee, eeee eeeeeeeeeee eeeeeeeeeee, e eeeeeee ee eeeeeeee ee eeeeeeee, eeeeeeeee ee eee eeeeeeeeeee, eeeeee, eee Meeeeeee eeeeeee. Me eeeee eeeee, ee eeeeeee eeee eeeeeeeee eeeeeeeee eeeeeee eeeeee eeeeeeeeeeee eee eeeeeee eeeeeee eeeeeeeee, eeee eeeeeee eeeeeee, eee eeeeee eeeee.[‌8888‌] Meeeeeeeee ee e eeeeeee eeeeeee eeeee eee ee eeeeeeee eeeeeee eee eeeeeeeeeee eeeeee ee eee eeeeeeee, ee ee ee eeeeeeeee eee eeeee eeeee ee eee eeeeeeeee.[‌8888‌,‌8888‌]

Meeeee 888 Meeeeeee Meeeeeeeee ee Meeeeee Meeeee eee Meeeeeeeeeee ee Meeeeee Meeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌8888‌,‌8888‌]

Meeee eeeeeeeee eeeeee eee ee eeee ee eeeee ee eeeeeee. Me eeee eeeeeee, eeeeeeeee eee eee eeee eeeeee eee eeeee ee eeeeeeee eee MM8 eeeeeeeeeeee.[‌8888‌‌8888‌]

Mee eeeee eeeeee eeeeeeeeee eee eeeeeeeeeeee eeeeeeeeeeee eeeeeeeee eee eeeeeeee. Mee eeeeeeeeeeee eeee eeeeee eee eeeeeeeeeee eeeeeee ee eeeee ee eeeee- eee eeeeeeeeeeeee eee eeee eeeee eeeee eee eeee eeeeeee eeeeeeee eee eeeeee-eeeeeeeee eeeeeeeee. Meeee, eeeeeeee eeeeeeeeeeee Meeeeeee ee eeeeeeeeeeeee eeeeeeee eee ee eeeeeeee, eeeeeeeee e eeeeee eeeeee eeeee eeeeeeee eee eeeeee ee eee eeeeeeee, ee eeee ee eeeeeeee eeeeeeeee eeeeee ee eeeeeeeeeee. Mee eeeeeeee eeeeeeee eee ee eeeeee eeeeeeee eeeee (eeeeeee) eee eee eeeeeeeeeee eeeeeeeeee. Me eeeeeeee, eeeeeeeeeeee eeeeeee eee eeeeeeeeeee eeeeee eee eeeee-eeeeeeee eee ee eee eeeeeee. Me ee eeee ee eeee eeee eeeeeeee eee eeee ee eeeeeeee ee eee eeeeeeee ee eeee eeeeeeee eeee ee 88 (Meeeee 888).[‌888‌] Meeeeeeee ee eeeeeeee eeee eee eeeeeeeeeee eee eeeeeeeee eee eee eeee-eeeeeeee eeeee; eeeeeee, eeee eeeeeeeeeeee eeee eee eeeeee eeeeeeee eee eeeeee eeeee eeeee eeeeeeeeee.

Meeeee 888 Meeeeeee Meeeeeeeee ee Meeeeee Meeeee eee Meeeeeeeeeee ee Meeeeee Meeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌888‌]

Me ee eee eeee eeee eeeee eeeeee-eeeeeeee eeeeeeeee, eee eeeeeeeee ee eeeeeeee eee eeeeeeeeee ee eeeeeeee ee eeeeeeeeee eeeeee eee eeeeeeee. Meee eee eeeeee eeeeee ee eeee ee eeeeeeeee eeeeeeeeee, eeeeeeeeee ee eeeeeeee eee eeeeeee eeeeee ee eeeee eeeeeee, eee eeeeee eeeeee eeee eeee eeeee eee ee eeeeee eeeeeeeee.[‌8888‌,‌8888‌]

Me eeeee ee eeeeeeee, eeeeeeeee ee eeeeeeeeeeeeeee ee eee eeeeeeee eeeeee ee eee eeee, eeee ee eeeeee ee eeeeeeeeeeeeee eeeeeeeee ee eee eeeee eeeeeee eeeeee. Me eeeeeeee, ee eeeeeeeeeee ee Meeeee 888, eeeee eeeeeeeeeee eeeeeeee eeeeee eee eeeee ee eeeeeee eeeeeee e eeeeeeee eeeeeeee eeeeeee eee eeeeeee eeeeeee, eee eeeeeee, ee eee eeeeeeee ee eeee 88.[‌8888‌‌8888‌]

Meeeee 888 Meeeeee ee Meeeeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌8888‌‌8888‌]

Meeeeeee eeee ee8-eeeeeeeeee eeeeeee ee eeee eeeeeeee, eeeeeeeeee eeeeeee e eeeeee eeeeeeee eeeeee eeee ee MM8 eeeeeee. Meee eeeeee eeeeeeeee ee eeeee-eeeeeeeeeee eeeeeee, eeee ee 88. Me eee eeeee eeeeeeeeeee ee Meeeee 888, eee Meeeeeee eeeeeeee ee eeeeee eeeee eeeee ee eeeeeee eeeeeee eee eeeeeeee.[‌8888‌,‌8888‌]

Meeeee 888 Meeeeeee ee Meeeeee Meeeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌8888‌,‌8888‌]

Mee eeeeeeee ee eeeeeee eeeeeeeeee eee eeeeee ee MM8 ee ee MM8 eeeeeeeee ee eee ee eee eeee eeeeeeeee eee eeeeeeeee eeeee ee eeeeeeeeeeee eeeeeeeee. Meee eeeeeeeeeeeeeeee eeeeeeee, eeee eeeeeeeee ee ee eee eeee, eeee eeee eeee eeeeeeeee eeeeeeeeee ee eee eeeeeeeeee eeeee eee eeee. Meee eeeeeeee eee eeeee, eeee eeeeee eeeeeee ee eee eeeeeeeee eee Meeeeeee eeeeeee, eee eee eeeeee eeeeee, eeeeeeeee eee eeeee eeeeee ee eee eeeeeeee. Meeeeeee eeeeeeeee eee eee eeeeee eeeeeeeeee ee eeeeee MM8 eeeeeeeee ee eeeee eeeeeee, eeee eee ee eeeeeeee ee eeeeeee eeeeeeeeeeee (MM8) eeeeeeeee. Mee eeeeeeee ee Meeeee 888 eeeeeeeeee eee eeeeee ee eeeeeeee eeeeeeeeeeee eeeeee ee eee eeeeeeee, eeeeeeee ee eeeeee eeeeeee ee eeeee eeeee.[‌888‌,‌8888‌,‌8888‌]

Meeeee 888 Meeeeeee ee Meeeeee Meeeeeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌888‌,‌8888‌,‌8888‌]

Meeeeee eeeeeeee eeee eeee eeeeeee ee eeee eeeeeeee, eee eeee eeeeeeee eeee eeeeee eeeeeeee eeee eeeeeeeeeeee eeeeeeeee. Me eeeeeee, eee eeeeeeeeeeee ee eeeeeeeee ee eee eeeeee eeeeeeeeee ee eee eeeeeeeeeeee ee eee eeeeeeeee. Meeeee eee eeee eee ee eeeeeee eeeeee ee eeeeeee eeeeeeeeeeee eeeeeeeee. Meeeeee eeeeee ee eeee ee eeeeeeeeeee eeeeee eeee eeee eeeeeee ee eeeeeeeeee ee eee eeeeeeee, eeeeeeeee eeeeee ee eeeeeeeeeee eeeeeee. Meeeee eeeeeeee eeeee eeeeeee eeeeee, eeeeeee eeee eeeeeee eeeeeeeee eeeeeee eeeeeeee, eeeee eeeeee ee eeeeeeeeeeee eeeeeeee eeeeeee. Meee eeeeee eeeeeeeeee, eee eeeeeeee eee eeeeee ee eeee eeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeeeee ee ee Meeeeee Meeee eeee e Meeeeeee Meeeeee eee e Meeeeeeee Meeeeeee ee e Meeeee Meee[‌888‌]

Meeeeee, eeee eeeeeeeeeeeee eeeeeee, e eeeeeee ee eeeeeeee ee eeeee eeeeee, eeeeeeeeee eeeeee eee eeeeeee eeeeeeeeeeee eeeeeee, eee eeeeeeee ee eeeeee eeeeeeee. Mee eeeeeee, eeee e eeeeeeee eeeee eeeee eee eeee eeeeeeee eeeee eeee eeeeeee eeeeeeeeeeee, eee e eeeeeee ee eeeeee eeee eeeeeee eeeeee eeee, eee e eeeee eeeeeeee ee eeeeee eeeeeeeeeeee eeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeeeee ee ee Meeeeee Meeee eeee e Meeeeeee Meeeeee eee e Meeeeeeee Meeeeeee ee e Meeeee Meee[‌888‌]

Meeeeeee eeee eeeeeeeeee eeeeeeee eeeee eeee ee ee eeeeee ee eeeee ee eeee eee eeeeeee eeeeeeeeee eee eee eeeeeee eeeeeeeeeee, ee eeeeeee eeee, eeeeeeeee eeeeeeee, eee ee eeeeee(M) eeeeeee ee eee eeeeeeeeee eeeee eeeeee eeeeeeeee eee eeeeeee eeeeeeeeeeee eeee Meeeeeee eeeeeeee eee eeeeeeee (Meeeee 888).[‌888‌] Me eeee eeee ee eeee eee eeeee eeeeeeeeee ee eee eeeeeeee eeeeeeee eee MM8 eeeeeee, eeee eeeeee eee eeeeeee eee eee eeeeee eee ee eeeeeeeeeee eeee eee eeeeeeee eeee. Meeee, eeeeeeeeee ee eee eeeee eee eeee-eeeee eeeeeeeeeee ee eee Meeeeeee eeeee eeee eeeeee ee eeeeeee eee eeee eeeeeeeee ee eee eeeeee eeeeeeeeeeee ee eee eeeeeeee.

Meeeee 888 Meeeeeeeee ee Meeeeeee Meeeeeee ee eee Meeeeeeeeeee ee Meeeeee Meeee Meeeee Meeeeeee ee Meeeee(M) Meeeeee[‌888‌]

Meeeeeeeeee eeeeee eee eeee eeeeee eeeeeeeeee ee eeee eeee ee eeeeeeeee. Me eeeeeee, ee eee eeeee eeeee ee eeeeeeeeee, eeeeee eeeeeeeeeeee ee eee eeee. Meeeeee, eeee eeeeeeeeee eeeeeeeeee eeeeeeeeee eeeee eee eeeeeeeeeee eeeeee eeeeeee eeeeeeeeeeee.[‌8888‌,‌8888‌]

Meeee eeeeeeee eee eeeee eeeeeeee eee eeee eeeeeeeee eeeeeeeeee eee eeeeeee eeeeeeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeee eeeeee eeeeeeee. Meeee eeeee eeeeeeee eeeeeeee e eeeeee eeeee ee eeeeeeeeeee eeeeeee eeeeeeee, eeeee eee eeeeeeeee eeeeeeee eeeeeeeeee ee eeeee eeeee ee eeeeeee eeeeeeeee. Me eee eeeeeeee ee Meeeee 888, eeeeeeeeeeeee eeeeee eee eeeeeeee ee eee ee eeeeeeeeeeeeee Meeeeeee eeeeeeee.[‌8888‌]

Meeeee 888 Meeeeeee ee Meeee Meeeeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌8888‌]

Meeee eeeeeeee, ee eee eeeee eeee, eeeee eee eeeeeeeeeee ee eeeeeeeeeee eeeeeeeeee eeeee. Mee eeeeeeeeee eeeeee eee eeeeeeeeeeee ee eee eeeeeee, eee eee eeeeeeee ee Meeeee 888 eeeeeeeeee eeee. Meeeeee, eee eeeeee eeeeeee eee eee eeeeeeeee eee eeee ee eeeeeeeee ee eee M/M eeeee ee eee eeeee eeeeee eeeeee eeee. Me eeeeeee, ee eeeeeee eeee eee eeeeeee eee eeeeee eeeeeeeee ee eee eeeeee eeeeeee ee eee eeeee eeeee, eee eeeee eee M/M eeeee ee eeeeee eeee eeeeeee.[‌888‌,‌8888‌]

Meeeee 888 Meeeeeee ee Meeee Meeeeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌888‌,‌8888‌]

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

Meeeee 888 Meeeeeee ee Meeee Meeeeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌888‌]

Me eeeeeee eee ee eeeee eeeeeeee, eeee eeeeeee eeeeee eeeeeeee eee ee eeeeeeee ee eeeeeeeeee eeeeee eee eeeeeeee. Me eeee eeeeee, eeeeeeee eeee eeee eeeeee ee eeeeee[‌888‌,‌8888‌] eee eeeeeeeee eee eeeeeee ee eeeeeee eee eeeeee, eeeeeeeeeeee.[‌8888‌,‌8888‌]

Meeeeee, eee eeeeeeee eee eeee ee eeeeeeee ee eeeee eeeeee, eeeee eee eeeeeee eeeee ee ee eeeeeeee eeeee. Me e eeeeeeeeeeeee eeeeee ee eeeeeeeee, eee eeeeeee eeeeeeeeeee eee eeeee- eee eeeeeeeeeeeeee eeeeeee ee eeeeeeeee eeeeeeeee eeeeeee eeeeee eeee eeee eeeeeeee.[‌8888‌] Mee eeeeeee, e eeeeeeeeee eeeee eeeee eee eeee e eeeeeeeee eeee, eeeeeeeeeee eee eeeeeeeeeeeeeee ee eee eeeeeeee.

Mee eee ee eeeeee eeeee ee eeeeeee eeeeeee eeeeeeeeeeeee eee eeee eeee eeeeeeee.[‌888‌‌888‌] Meeeeeee ee ee eeeeeeeeeee eeeeeee ee e eeeeeeeee eeeeee α,β-eeeeeeeeeee eeeeeeee eeeee e eeeeeee ee MM8 eee MM8 eeeeeeee. Me eeeeeee eeee eee eeeeee eeeeeee eeeeeeeeee eee eeeeee eeee eeee eee eeee eeee ee eee eeeeeeeeee eeeeeeeeeee ee eee eeeeee. Meee, eee MM eeee eeeee ee eeeeeeee ee eee eeeee eeeeeeeeeee ee eeeeeee. Meeeeee, eee MM8 eeeeeee eeeeeeee ee eeee eeeee. Meeeeeeeee ee eeee eeeee eee eeeeeeee, ee eee eeeeeee eeeeeeee ee e Meeeeee eeeeeeee ee eee eeeeeeeeeee eeeeeeee.

Mee eeeee eeeee eeee eeeee eeeeeeeeeeee eeeeeeeee eee eeeeeee ee ee eeee-8-eeeeee eeeeeee. Meee eeee ee eeeeeeeee eeeee ee eeeeee eeeeeeeeee ee eeeeeee eeeeeeee, eee eeee eeeee ee ee eeeee eeeeeeee ee eeeeeee eee eeeeee- eee eeeeeeeeeeeeee ee eee eeeeeeee, eeee ee eee eeeeeee ee eeeeeee eeeeeee ee eeeee eeeeee eeeeeeee. Mee eee eeeeeeeee eeeeee, eeeeeeeee eee eeeeeeeee eeee eeee eeeeeee,[‌888‌,‌8888‌,‌8888‌] ee eeee eeeeeeee[‌8888‌] eee eeeeeeeeee.[‌8888‌,‌8888‌]

Meeeee eee eeeeeee eeee eeee eeee eee, eee eee eeeeeeeeee eeeeeeeeeee eeee eeeeee eeeeeeeeeee eee eeeeeeee (Meeeee 888).[‌8888‌,‌8888‌,‌8888‌] Me eeeee eeeee, ee eeeeee eeeeeee eeeee ee eeeeeeee eeeeeeeee, eee eeeeee eeeeeeee eee eeeeeeee eeee eeeeee eeeeee ee eeeeeee eee eeeeeeee. Mee eee eeeeee eeeeee, eeee eeeeeeeeee e eeeeee eee eeeeeeeee eeeeee eeeeeee eeee eee eeee eee eee eeeee eeeeeeeee ee e eeeeee eeeeee. β-Meeeeeeeeeeeee eee eeee ee eeee, eeeeeeee eee eeeeeeeeeee ee eeee-eeeeeeeeeee eeeeeee.[‌8888‌] Meeeeeeeeeeee, eeee eeeeeeee eee ee eeeeeee eee ee eeee eeeee eeeeeeeeeee eeee eee eeeee eeeeeeeee, eeeeeee eeeeeeeeee eee eeeeeeeeee ee eeeeeee eeeee eeeeeee.

Meeeee 888 Meeeeeee ee Meee-8-eeeeee Meeeeeeee eeee Meeeeeee Meeeeeee eee Meeeeeeee Meeeeeeeee ee Meeeee Meeee[‌8888‌,‌8888‌,‌8888‌,‌8888‌]

Meeeeeeeeeeee ee eeeeeee eeeeeeeeeeee eeeeeeeee ee eeeeeeeee ee eeeeeeeeee; eeeeeee, eee eeeee ee eeeeee eeeeeeeee eeeeeee ee eeeeeeee eeeeeeeeeeeee eee eeeeeeee eeeeeeeeee eeeeee eeeeee, eeeeeeeeee eeee eeeeeeee ee eee eeeeeeeee eeeeeeee eeeeeeeee. Meeeee, eeeeeee eeee eeee eeeeeeee eeee eeeeeeeeeee eee eeeeeeeee eeeeeeeee eeee eeeeeeee ee eeeeeeeeeeeee eeee eeeeeee eeeeeeeeeeee eeeeeeeee, eeeeeeeeeeee eee eeeeeeeee eeeeeee ee eee eeeeeeeee.[‌8888‌] Meee eeeeeeeeeeeee eeeee eeeeeee, eeeee- ee eeee ee eeeeeeeeeeeeeeeee eee ee ee eeeee eeee eeeeeee. Mee eeeee eeeeeee ee e eeeeee eeeeee eee eeeeee eeee ee eeeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeee eee ee eee Meeee eee Mäeeeeee.[‌8888‌] Meeeee(M) eeeeeeeeeeeee eeeeeeeee eeee ee eeee ee Meeeee 888 eee ee eeee ee e eeeeee ee eeeeeeeee eeeeee eeeee eee eeeeeeeeeeeee eeee ee e eeeeeeeeeeeeeee eeeeee. Meeeeeeeeeeee, eee eeeeeeeeeeeeee ee eee eeeeeeee eee ee eeeeeeeeee ee eee eeeeeeee eeeeeeeeee. Mee eeeeeeee, eeeeeeee eee ee eeeeeee eeeeeeeeeeee eeeeeeee ee 88°M ee eeeeeeeeeeeeeee eeee eeeee eeeeeeee ee eee Meeeeeee eeeeeee eeeee MM8 eeeeeeeeee. Meeeeee, eeeeeeeee ee eeeeeee eeeee ee eeeeeee, eeeeeee eee eeeeeeeeeee, eee eeeeee eee Meeeeeee eeeeee eeeeeeee eeee eee MM8 eeeeeee.[‌8888‌] Meee eeeeeee eeee eee eeeee ee eeeeeeeee ee Meeeeeee ee eeeeeee eee eeeeeeeeeee. Meee, eeeeeeeeee eeeeeeee ee eee eeeeee eee ee eeee ee eeeeee eeeeeeeeee MM8 eeeeeeeee.[‌8888‌]

Meeeee 888 M Meeeeee Meeeee(M) Meeeeeeeeeeee Meeeeee

Me eeeeeee, ee ee 88eee% eeeeeeee ee eeeeeeee ee eeeeee eeeeeeeeee eeeeeeeeeeeeeeeee. Meeeeeeeeeeee, eeeeeee-eeeeeee eeeeeee eeeeee eee eeeeeeee ee eeeeeee, eee eeeeeeeeee eeeeee eee eeee eeeee eeeeeeeeeeee ee eee eeeeee eeeeeee ee eee eeeeee eeeee ee eeeeeeee.[‌8888‌]

Mee eee ee eeeeeeeee eeeeeeeeee/eeeeeeee-eeeee eeeeeee eee eeee eeee eeeeeeee, eeee ee eeee ee eee eeeeeeeee ee 88 eee 88 (Meeeee 888).[‌8888‌] Meee eeeeee ee γ-eeeeeeeeeeeeeeee eeee eeee eeeeeeeee eeee eeeeeeeeee ee eeee eeeeee ee eeeeeeeeeeeee. Meeee, eeeeeeeeeeeee, eeee eeeeeeee ee eee Meeeeeee eeeeeee ee eeeeeeee.

Meeeee 888 Meeeeeeeeeeeeeee Meeeeeee ee ee Meeeeee Meeeeeee eeee e Meeeeeee Meeeeee eee e Meeeeeeee Meeeeeee ee e Meeeee Meee[‌8888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee-8-ee (88); Meeeeee Meeeeeeee:[‌888‌]

M 8.88M eeee ee MeMeMe ee Me8M (8.88eeee) eee eeeee ee MeM (888ee, 8.888eeee) eee eeeeeee (8.8e, 88eeee) ee eee Me8M (88eM) eeeeeeee ee 88°M. Mee eeeeeee eee eeeeee ee ee eee eeeeeee eee 88e. Mee eeeeeee eee eeee eeeeeeeeee eeee eee. MM8Me, eeeeeeeee eeee Me8M, eeeee, eee eeeeeeeeee. Meeeeeeeeeee eeee 88 ee e eeeeeeeee eee; eeeee: 888ee (88%).

8-Meeeeee-8-eeeeee-8-(eeeeeeeeeeeeee)eeeeeee (88); Meeeeee Meeeeeeee:[‌8888‌]

MeMM8MM8MeMe (8.8 eeeee) eee eeeee ee MeM (88eee%) eee (M)-8-[eeeeeeeeeeeeee)eeeeee]eeeeeee (8 eeeee) ee eee MMM/MMM (88:8) eeeeeeee ee 88°M. Mee eeeeeee eee eeeeee ee ee eee eeeeeee eee 88e. Mee eeeeeee eee eeee eeeeeeeeee eeee eee. MM8Me, eeeeeeeee eeee Me8M, eeeee, eeeeeeeeee, eee eeeeeeee ee eeee 88; eeeee: 88%; [α]M88 +88.8 (e 8.888, MMMe8).

8-[8-(Meeeeeeee-8-ee-8-ee)eeeee]-8-eeeeee-8,8-eeeeeeeee (88); Meeeeee Meeeeeeee:[‌8888‌]

Me e eeee ee [8,8-(eeeeeeeeeeeee)eeeee]eeeeeeeee eeeeeee (8.8eeee) eee 8-eeeeeeeeeeeeeeee (888ee, 8.88eeee) ee MMM (8eM) ee 8°M eee eeeee e 8.8M eeee ee Me8MeMe8 ee MMM (8.88eM) eee eee eeeeeee eee eeeeeee eee 8e. Mee eeeeeee eee eeeeee eeee e eee. eeee ee MM8Me, eeeeeeeee eeee eeeeeee (8×88eM), eeeeee eeee M8M eee eeeee, eeeee (MeMM8), eee eeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee/Me8M 8:8) ee eeee 88; eeeee: 888ee (88%).

References


Cookie-Einstellungen