Science of Synthesis

Matteson, D. S., Science of Synthesis, (2005) 6, 37.

In early work, it was found that borane–triethylamine hydroborates simple alkenes at 200°C in an autoclave.[‌133‌] It was suggested that the complex has to dissociate to form free borane before it can attack the alkene. However, there is evidence that full dissociation does not always occur before the trihydroborane unit is transferred from the borane complex to the alkene, inasmuch as hydroboration with chiral borane–amines shows a small degree of asymmetric induction.[‌158‌] Despite this, clearly the amine has to release borane to a considerable degree en route to the transition state. Steric hindrance can “loosen” the hydroborane–amine complex and allow efficient hydroboration under mild conditions, as illustrated by the discovery that tert-butylborane–trimethylamine readily hydroborates alkenes and alkynes in about 2 hours at 60°C.[‌159‌]

Me eeeee eeeeeee ee e eeeeee–eeeee eeee ee ee eeeeee eeeeeeeeeeeee eeeee (eeeeeee eee eeeee eeeeeee ee e eeee eeee) ee eeeeee–eeeeeeeeeeeee.[‌888‌] Mee eeeeeee ee eeeeeeee eeee eeeeee eeeeeeeeeee, eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee, eee eeeeeee ee eeeeeeeeeeeeeee ee 8°M. Me eeeeeeee ee eee eeeeeeee ee e eeeeeee eee eee eeeeeeeeeeeee ee eeeeeee, eeeeee–eeeeeeeeeeeee ee eeee ee eeeeee eeeeeeee eeeee eee eeeeeeeee, eeeeeee, eeeeeeeeee eeeee, eeeeee, eee eeee eeeeeeeeee.

Mee eeeeeeeeeeee ee 8-eeeeeeeeeeeeeeee, M,M-eeeeeeeeeeeeee, eee M,M-eeeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeee eee eeeeeeeee eee eeeeeeeeeeee eeeeeee eeee eeeee ee eeeeee–eeeeeeeeeeeeee, eee eeeee eeee ee eeeeee eeee eeeeeee eeeeeeeeee eeeeeeeeeeeeee eee eeeeeeeeee.[‌888‌] Meeeeeeeeeeee eeee eeeeeeeeee eee eeeee ee eeeeeeeeeeeee ee eee-8-eee ee eeeeee–eeeeeeeeeeeee ee eeeeee–eeeeeeee eeeeeee eeeeeee,[‌888‌] eeeeeeeeee eeee eeeeeeeeeeee ee eee eeeeee eeeeeee ee eeeeee ee eeeeeeee eeeeee eeeeeeeeeeeee eee eeee eeeee.[‌888‌] Meeeeee, ee eeeeeee eeeee, eeee eeeeeeeee eeeeeeeeee ee eeeeeeeeeee, eee ee eee eeeeee eeeeeeee ee eeeeeee eee eeeeeeeeeeee eeeeeee.

Meeeeeeeeeeeeeeeeeee, eeeeeee eeeee ee eeeeee eeeee eeeeee, eeeeeee e eeeeee ee eeeeee–eeeeee [MM8•M(MMM)M88], eeee eeee e eeee eeeee ee eeeeee eeeeeeee ee eeeeeeeeeeeee eeeeee.[‌888‌] Meeee eeeeee–eeeeeeeee eeeeee eee eeeeeeee ee eeeeeee eeeeeeee eeee e eeeeeeee ee eee eeeeeeeee eeeee ee eeeeeee eeeee ee −88°M. Meeee eeeeeeee eeeeee eeeeeee eeeee-, eeeeeeeee-, eeee-eeeee-, eee eeeeeeeeeeeee ee eeee ee eeeeeeeeee, eeeeeeeeee, eee eeeeeeeeeee. Meee eeeeeeeee eee eee-eeeeee eeeeeeeeeee eeeeee, eee eeeeeee eeeeee eeeeeee ee eee eeeeeeeeee ee eee eeeeeeeeeee ee eeee eeeeeeee ee eeeee-eeeeeee eeeeeeeeee.

Meeee ee eeeeeeeeeee eeeeeee,[‌888‌,‌888‌,‌888‌] M-eeeee-M-eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeeeeee eeeeee ee ee eeeeeeeeee eeeeeeeee ee eeeeee eeeeeeee eee eeeeeeeeeeeee eee eeee eeee eeee eeeeeee ee eeeeeeeeeeee eeeeee.[‌88‌,‌888‌] Meeeee–eeeeeeeeeeeeeeeeeeeeeeee eeeee e eeeeee eeeeee eeeeee eeee ee 8.8 M ee eeeeeeeeeeeeee eee ee eeeeee eeeeeeeeeeee ee 88°M eeeee ee eeeee eeeeeeeeee.[‌88‌] Meeeeeeeeeeeee eeee eeee eeeeeee eee eeee ee eeeeeee ee eeeeeee, eee eeee ee eeeeeeeeeeeeeee ee eeee-eeeee eeeeee eeeee. Meeeeeee eeeeeee eee eeeeeeeeeeee ee eee eeeeeeeeeeeeee eeeee ee eeeee 8 eeeee ee 88°M, eee eeeeeeeeeee eee 8-eeeeeeeee-8-eee eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeeeeeeeee eeeeeee, eee eeee eee eeeeeeeeeeeeeee eeee eeeeee; α-eeeeee eee 8,8-eeeeeeeeeee-8-eee eeeee eeeeeeeeeeeeeeee eeee eeeeeee. Mee eeeeeeee eeeee ee eeee eeeeeeeee eee eeeeeeee ee eee eeeee eeeee ee eeeeeeeeeeeeee. Meeeeeeeeeeeeee eee e eeeeeeeeee eeeeeeeee eeeeee ee eee eeeeeeeeeeeee ee eeeeeeee eeeeeee, eee eeeeeeeee eeeeee–eeeee eeeeeeee eee eeee eeee 88 eeeee ee eeee eeeeeee, eeeeeeee α-eeeeee eee 8,8-eeeeeeeeeee-8-eee eeeee eeeeeeeeeeeeeeee eeeeeee. Mee(eeeeeeeeeeeeeee)eeeeee, eeeeeeeeeeeeeeeeee, 8-eeeeeeeeeee[8.8.8]eeeeee, eee eeeee eeeeeeeeeeeeee eee eeeeeeee eeee eeeeeeeeeee ee eeeeeee eee eee ee eeee ee eee eeeeeeee ee eee eeeee ee, ee eee eeee ee eeeee eeeeeee, eeeeeeeeeeee. Mee eeeee eeee eee eeeeeeeee eeee eee eeeee eeeeeeeee ee eeeeeeeeeeeee eee ee eeeeeeeee eee eee eeeee eeeeeeeeee eeee eeeeeee eeee eee eeeeeeeeee eeee eeee. Meeeee–M-eeeee-M-eeeeeeeeeeeeeeee (‌88‌) ee e eeeeee eee ee 8.8 M ee eeeeee.[‌888‌] Mee eee ee e eeeeeeeeeeeee eeeee eee eeeeee eeeeeee, e.e. ee eeee eeeee-8-ee (‌88‌) eee eeeeeeeeeeee (‌88‌), eee e eeeeeeee eeeee eee eee eeeee ee eeeeeeeeee eeeeee eeee eeeee eeee eeeeee eeee eeee eeeeeeeee (‌Meeeee 88‌).[‌888‌] Meeeeeee eeeeeeeeee eee eeeeeeeee eee eee eee ee eeee eeeeeee ee eee eeeeeeeeeee ee eee(eeeeeeeeeeeeeee)eeeeee, (8M)-8-eeeeeeeeeeeeeeeeee, 8-eeeeeeeeeee[8.8.8]eeeeee, eeeeeeeeeeeeeeeeee, eee eee(8,8-eeeeeeeeeeeeee)eeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee Mee-8-eee eee Meeeeeeeeee eeee Meeeee–M-Meeee-M-eeeeeeeeeeeeeeee[‌888‌,‌888‌]

Meeeee–M,M-eeeeeeeeeeeeeeeeee ee e eeeee, ee 88–88°M. Meeeeeee ee eeeeeeeee eeee eeee eeeeeee ee eeee ee ee ee eeeeee eeeee eee eeeeeee eeeee, eee eee eeeeeeeee eeeeeee eeeeeeeeeeee eeee eeeeeeeeee eeeeeee. Mee eeeeeee ee eeee eeeeeeeeeee eeeeee ee e eeeeeee eeee eee eeeeeee-eeee eeeeeeee.[‌888‌] Mee eeee ee eeeeeeeeee ee eeeeeeee eeeee eeee eeeeeee eeeeeeeeeee eeeeeeeee ee eee eeeeeee eeee eeeeeeee eeeeeeeeeee, eee eeeeeee ee ee e eeeee ee ee e eeee eeeeeeeeee eeeeeeeee eeeeeee eeee eee eeeee eeeeee eeeeee–eeeeeeeeeeeeee eeeeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee eeee eeeeee–eeeeee eeeeeee eee eeee-eeeeeeeeeeeee ee eeeeee-eeeeeee eeeeee eeeeee–eeeeeee eeeeee eeeeee e M=M eeee ee ee eeeeeeee eeeeeeee; eeee eeeeeeee eeeee- eee eeeeeeeeeeeeeeee eeeeee eeeeeeeeeeeee eeee eee ee eeeeeeee ee α-eeeee eeeeeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

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

Mee-8-eee (8.88 e, 88 eeee) eee eeeee eeeeeeee eeee e eeeeee ee 8 eee ee e eeee ee eeeeee–M-eeeee-M-eeeeeeeeeeeeeeee (8.88 eM, 8.8 eeee) ee eeeeeeeeee eeeee MMM eeeeeee ee 8°M eeeee M8 (eee eeeeeeee ee eeeeeeeeee MM eeeeeeee, e eeeeeeee eeeeee ee eeeeeeee eee eeeeeeeeee eeeeeeee ee eee eeeeeee). Meeee 8 e ee 88°M, M8M eee eeeee eee eee eeeeeee eee eeeeee ee 88°M. 8 M ee MeMM (8 eM) eee eeeee, eeeeeeee ee eeeeeeee eeeeeeee ee 88% M8M8 (8 eM) eeee e eeeeee ee 88 eee. Mee eeeeeee eee eeeeeee ee 88°M eee 8 e ee eeeeee eeeeeeeeee. Meeee eeeeeee ee ee, eee eeeeee eeee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee M8MM8 eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeeeee eeee 8 M MMe ee eeeeeee eee eeeee, eeee eeeeee eeee eeeee, eee eeeee (MeMM8). Mee eeeee-8-ee/eeeee-8-ee eeeee eee 88:8; eeeee eeeee: 88%. Meee: eee eeee eeee ee eeeeee eee eeeee eee eee eeeeeeee ee eee eeeeeeeeee eeeeeeeeee.

Meeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeeee eee eeeeeeeeeee eee eeee ee eeee eeeeeeeee eee eeeeeeeeeeeee ee eee-8-eee, eeeeee eeee eee eeeee ee eeeeeeeee eee eeeeeeee ee 8:8 [eeeeee–M-eeeee-M-eeeeeeeeeeeeeeee (8.88 eM, 8.8 eeee) eee eeeeeeeeeee (8.88 e, 88 eeee)] eee eee eeeeeeee eeee eee 8 e ee 88°M. Meeee eeeeeeeee eee eeeeeeeeee eeee eeeeeeee, eee eeeeeee eeeee eee eeeeeee eeee 8 M ee MMe ee eeeeeee eee eeeee, eee eeee eeeeeeeeeeee. Mee MeMM eee eeeeeeee ee eeeee eeeeeeeeeeeeee eeeeeee e eeeee eee ee eeeeee eee; eeeee: 8.88 e (88%).

Mee eee eeeeeeee ee M-eeeee-M-eeeeeeeeeeeeeeee, eee eeeeeee eeeee eee eeee eeeee eeee 8 M MMM eee eeeeeeeee eeee Me8M. Mee eeeee eeeee eeeeeeeee 8% MeMM ee MM, eee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8); eeeee: 8.88 e (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e8, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 88.