Science of Synthesis

Matteson, D. S., Science of Synthesis, (2005) 6, 35.

Borane–trimethylamine, the simple complex of the Lewis base trimethylamine with the Lewis acid trihydroborane, was the first of its type to be discovered,[‌131‌] and it is now a commercially available reagent. Hydroborane–amines are generally stable and resistant to hydrolysis and air oxidation.[‌132‌] With unhindered boranes and unhindered alkylamines of usual basicity, the complexes are usually too stable to transfer borane to an alkene unless strongly heated.[‌133‌] Borane–amine chemistry has been reviewed.[‌134‌] This section does not include the chemistry of bis(pyrazolyl)borates,[‌135‌] lithium (dialkylamino)borohydrides,[‌136‌] or other borane–amine anions that are classified as hydroborates. In early work, the reduction of aldehydes and ketones by borane–amines was patented.[‌137‌] The reduction of 4-tert-butylcyclohexanone with borane–trimethylamine is slow, but greatly accelerated by boron trifluoride–diethyl ether complex.[‌138‌] Weakly basic or highly hindered amines form dissociable borane complexes that can be useful hydroborating agents.[‌139‌,‌140‌]

Mee eeeee eeeeee ee eee eeeeee, eeeeee–eeeeeee [MM8•MM8], ee eee eeeeeeee ee eee eeeeeeee ee eeeeeee eeee eeeeeeee;[‌888‌] eeee eeeeeee eee “eeeeeeeeeee ee eeeeeeee” [(M8M)8MM8+MM8−] eeeeeee (eee Meeeeee ‌8.8.8.88‌). Meeeeeee eeee eeeee eeee eeeeeeeeeee eeee, eee e eeeeeeeeeeeeeee eeeeeeeee ee eeeeee–eeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeeee eeee eeeeeeee eeeeeeee ee eeeeeee eeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeee–Meeeeee[‌888‌]

Me eeeeeeee ee eee eeeeeee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeeee ee eeeeee–eeeeeee, eeeeee–eeeeeeeeeee eee ee eeeeeeee eeeeeeee eeee eee eeeee eee eee eeeeee.[‌888‌] Mee eeeeeee, eeeeee–eeeeeeeeeeeee eee ee eeeeeeee ee eeeeeee eeeeeee eeeeeeee eeee eeeeee eeeeeeeeeeeee, eee ee eee ee eeeeeeee ee eeeeee eeeeeeeeeeee. Meeeeeee eeeeee–eeeeeeeeeeeee (8 eM) ee eeeee eeee M8M (8 eM) eee 8 eeee eeeeeeee eeee eeeeee eeeeeeee (8 eM) (<8.8% ee eee eeeeeeeeeee eeeeee). Meeee eeeeee eeeeee–eeeeeeeeeeeeee eee ee eeeeeeeee eeeeeeee,[‌888‌] eee ee ee eeeeeee eeeeee ee eeeeeee eeeeee–eeeeee eeee e eeeeee–eeeeeee eeeee ee e eeeeee–eeeeeeee eeeeeee eeeeeee.[‌888‌,‌888‌,‌888‌] Mee eee eeeeeeeee ee eeeeee–eeeeeeee, eeeeee–eeeeeeeee, eee eeeeeee eeeeeeeeeeee eeeeeee eeee eeeeee–eeeee eeeeeeeee, ee eeeeee ee eee eeeee eeeeeee eeeeee ee eeeeeee, ee eee eeeeeeee eeee ee eeeeeeeeeee ee eeeeeeeee ee eeeeee eeeeee.[‌888‌]

Meeeeeeee ee eeeeeeeeeeeee eeeeeeeeeeeeee eeee eeeeee eeeeeeeeeee, ee eeeeeeeeeeeee, ee eeeeeee eeeee eeeeeee eee eeeeeeeeeeeee eeeeee–eeeeee (MM8•MM88 ee MM8•MM88). Me eeeeeeeeee eeeeeeee eeeeeeee eeeeee eeeeee eee eeeeeeee ee eee eeeeeeeeeeeee.[‌888‌] Meeeeeee ee eeeeeeeeeeeeee eeeeeeeeeeeee eeee eeeeee eeeeeeeeeeeeeeee eeeeee eeeeeeeeeee–eeeeeeeeeeeeee (MM8MM•MMe8); eee eeeeeeeeeeeee eeeeeeeeeee–eeeeee eeee eeee eeeeeeeee eeeeeeee eeee eeeeeeeeeeeee, eeeeeeeeeee, eeeeeeee, eee eeeeeee eeeeeeeeeeeeee.[‌888‌] Meeeee eeeeeeeee eeee ee eeeeee–eeeeeeeeeeeee, ee eeee ee eeeeee–eeeeeeee eee eeeeeee eeeeeeeee, eeee eeee eeee ee eee eeeeeeeee ee eeeeee eeeeeeeeeee eeee eeeeee ee eee eeeeeeee ee eee eeeee (‌Meeeee 88‌).[‌888‌,‌888‌] Meeeee eeeeeeeeeee eeee ee eeeee ee eeeeee eeeeee eeeeeee eeee eeeeee eee eeeeee–eeeee.[‌888‌] Meeeeee eeeeeeee eeeeeee eeeeeeeeee ee eeeeeee eeeeee ee eee eeeeeeee ee ee eeeee, eeeeeee eee eeeee eeeeeeee ee eeeeeeeeeeeeeee–eeeeee[‌888‌–‌888‌] eee eeeeeeeeeeeeeeee–eeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeee Meeeee ee Meeeee–Meeeee[‌888‌,‌888‌,‌888‌]

Mee eeeeeeeee ee eeeeeee (eeeeeeeeeeee)eeeeeeeeeeee [Me(M88MMM8)]eeee eeeeee eeeeeee ee eeeeeeeeeeeeeee ee 8°M eeeeeee ee eeeeeeeeeee ee eee eeeee ee eeee eee eeeeee–eeeeeee(eeeeee)eeeee (MM8•MMeM88).[‌888‌] Meeeeeee ee eeeeeeeeeeeeeeee(eeeeeeeeeeeeeee)eeeeee [(M8M)8MMMe8] eeee eeeeeeeeeeeeeeee, ee 8-eeeeeeeeeee[8.8.8]eeeeee, eeeeee eee eeeeeeeeeee eeeeee–eeeee [(M8M)8MM•MMe8MeMe8 ee (M8M)8MM8•MMe8(8-MMM)], eeeeee ee eeeee eee ee eeeeeeeeee ee eee(eeeeeeeeeeeeeee)eeeeee–eeeeeeeeeeeee [(M8M)8MM•MMMe8].[‌888‌] Meeeeeeee ee eeee eeeeee–eeeee eeee eeeeeeeee eeeeeeeee eeeeeeee ee eeee eee eeeeeeeee eeee {M[(M8M)8MM•MMe8]}, eeeee eeee eeeeeeee eeeee eeeeeee (M8M) ee eeeeeeeee eeee eee eeeeeeeeeeeee eee(eeeeeeeeeeeeeee)eeeeee–eeeeeeeeeeeee [(M8M)8MM•MMe8M8].

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

‌Meeeee 88‌ Meeeeeeeeee ee Meeeee–Meeee Meeeeeeee eeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee–Meeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee ee eeeeee eeeee eee eeeeee ee eeeeeeee ee eeeeee eeeeeeeeeeeee ee e eeeee eeee eeeeee. Meeeeeeeee ee eeeeeeee eeeeee ee eeeeeee eee ee ee eeeeeeeee eeee, eee eee eeeeeeee eeee ee eeeee eee eeee eeeee eeeeeee eeeeeeee eeeeee eeee eeeeeee e eeeee eeee eeeeee eeee eeeeeee eeeeee eeeeeeee eee eeeeeeeeee. Meeeeeee eee e eeeeeeeeeeeeee eeeeeeeeee “eeeeee eeeee” eeee, eee eeee ee eeeeeeeeeeeeee eeee eee eeeeee ee eeeeeee eee eee eeeeeeee eeeeee ee eeee.[‌88‌] Meeeee eeeeeeee ee eeeeeeeeeeee eeeeeeeee eee eeeee eeeeeeeeeee ee eeeeeee eeee eee.

Mee eeee eeeee (88 eeee) eee eeeeee ee e eeeeeee ee eeeeeeee eeee, eeeee eee eeeeeeee eeee e eeeeeeee eeeeeeee eee eee ee eeeee eeee e eeeeeeee eeeee eee eee eee eeeeee ee ee eee eeee ee 8°M. M eeeeee eeeeeee eee eee eee eeeeee eeeeeee e eeeee ee Me eeeeeee eeee MMM (88 eM), eeee e eeeee eeee ee eee eeeeeeeeee eeeeeee e eeeee Me eeeeeee. M8M8 (‌8‌) eee eeeeeeeee ee eeeeeeeee ee Meeeeee ‌8.8.8.8.8‌ eee eeeeee eeee eee eeeee. Meeeee M8M8 eee eeeeeeee ee eee eeeee eee eeeeeeee ee eee MMM. Meee eee eeeeeeeeeeeee eeeeeee ee. 8 M, M8M8 eeeeeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeee eeeeeeeee ee eeeee 88°M eeeeee eeeeeeeeeeeee eee eeeeeeee. Mee eeeeee eeeeeee ee eee eeeeee–eeeee eee eeeeeeeee eeee eee eeeeee ee M8 eeeeeee ee eeee eeeeeeeeee.

References

Meeeeee Meeeeeeeeee

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