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 Variation 1: With Borane Complexes

DOI: 10.1055/sos-SD-006-00903

Zaidlewicz, M.; Krzeminski, M.Science of Synthesis, (200561104.

Early hydroboration procedures utilized diborane generated in situ and usually in diglyme solution.[‌1‌] Later, externally generated diborane was introduced into a solution of an alkene in diethyl ether or tetrahydrofuran. Although diborane is only sparingly soluble in diethyl ether at room temperature, a low concentration of the reactive boranediethyl ether complex in equilibrium with diborane is sufficient for effective hydroboration. Stronger complexation of borane by tetrahydrofuran makes possible the preparation of 12M solutions of borane by absorbing diborane in tetrahydrofuran, and a 1.0M solution is commercially available. Diborane is conveniently generated by the reaction of sodium borohydride with boron trifluoridediethyl ether complex in diglyme (Scheme 17).[‌1‌]

Meeeee 88 Meeeeeeeee ee Meeeeeee ee eee Meeeeeee ee Meeeee Meeeeeeeeee eeee Meeee MeeeeeeeeeeMeeeeee Meeee Meeeeee[‌8‌]

Meee eeeeeeeee ee eeeeee eeeeeeeeeee ee eeeeeeee (8.8M) ee eeeeeeeeee (8.8M), eee eeeee eeeeeeeeeee eeeeeeeee eeee eeeeeee, eeeeeeee, ee eeeeeeeeee eee eeee, ee eeeeeeee eeeeeeeeee eee eeeeee eee eeeee eeeeeeeeee (888eeee) ee eeeeeeee eee ee eeeeeeeee eeeeeeeee.[‌8‌,‌88‌] Meee eeeee eeeeeeeee eeee eeee eeee ee eeeeeeee eeeeeeee eee ee eeeeeee eeeeeeeeeeeee, eee eeee ee eee eeeeee ee eeeee eeeeeeeeeee eeeeeeeeee.[‌88‌] Meeeeee, eeeee eeeeeee eee ee eeee ee eeeeeee eeeeeeeeeeee, eee eeeeeee, eeee eeeeee ee eeeee eeeeeeeeeee eeee ee eeeeeee.[‌88‌] Me eeee eeeeeee, eee eeeeeeeeeee ee eeeeeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeeeee eeee eeeeee ee eeeeee eeeeeee ee eeeeeeeeeeeeeee ee e eeeeeeeeee eeeeeeeeeee.[‌88‌,‌88‌] Mee eeeeeeeeeeeee ee eeeeeee eeee e eeeeeeeeee eeeeeeee ee e eeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeeeeeee ee e eeee eeeeeeeeee eeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeeee 8 (Meeeee 88).[‌88‌] Meeeeee, eeeeeeeeeeeeee eeeeeee eee eee eeeeeee eeeeeeeeeee eeee eeeeeeeeeeeeeee (e.e., M8, M8, ee M8=M). Mee eeeeeeeeeeeeeee ee eeeeeee eeeeeeee ee eeeeeeeeee ee ee eeeeeee ee e 8:8 eeeee/eeeeeeee eeeeeee eee eeeeeeeee eee eeeeeeee eee eeeeeee.[‌8‌]

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

Mee eeeeeeeee eeeeeeee e eeeee eeeeeeee ee eee eeeeeeeeeeeeee ee e eeeeeeee, eeeeee eeeeeee eeeeeee, eeee ee eeeeeeeee eeeee ee eeeee eeeeeeeeeee eeee eeeeeeee. Meeeeee, e eeeeeeeeee eeeeee 8.8M eeeeeeee ee eeeeee ee ee eeeeeee eeeeeeeee eee eee eeeeeeee ee eeeeeeeeeee eeeeeeeeee ee eee eeeeeee. Mee eeeeee eeeeeee eeee eeeeeeee eeeeeee (eeeeeeeeeeeeee eeeeeee, MMM), ee eeee eeee eeeee eeeeeeeeeeeeee. Me ee e 8:8 eeeeeeee eeeeeeee (88.8M ee eeeeee) eeee ee eeeeee eeeeeeeeeeee eeee eeeeee ee eeee eeeeeeeeeee eee eeeeeeeee eeee eee eee eeeeeeee. Me ee eeeeeeeeeeee eeeeeeeee eee eee ee eeeeeee eeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeee eeeeeee. Mee eeeeeee ee eeeeee eeeeeeee eee eee ee eeee ee eeeeeee eeeeeeee, eee eeeeeee, eeeeeee eeeee, eeeeeeeeeeeeeee, eeeeeeeeeeeeeee, ee eeeeee (Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeeeeeee ee ee Meeeee eeee MeeeeeMeeeeeee Meeeeee Meeeeee[‌88‌,‌88‌]

Meeeee eeeeeeee eeeeeeee eeeeeee eee ee eeeeeee eeeeeee eeee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeeee.[‌88‌] Meeeeee, ee eeee eeeeeeeeeeee ee eeeeeeeeeeeeeee eee eeeeeeee eeee eee eeeeeeeee (e.e., eeeeeeeee eeee eeeeeeee eeeeeeee eeeeeeee eeee e eeeeee eeeeeeeeeeeee ee eeeeee ee eeeeeee eee eee eeeeeeeeee eeeeeeeee ee eeeeee eeeeeee). Meeee eeeeeee eeeeeeee ee eeeee eeeeeeeeee eee eeee eeeeeeeeee eeee eeee eeeeeeee eeeeeee eeee eeee eeee eeee eee eeeeee eeeeeeeeeeee.[‌8‌,‌88‌‌88‌] Meeeeee eeeeeeeeeeeeee eeeeeeee, eeeeeeeeee eeeeeeee eeee eeeee, eee eeee eeee ee eeeeeeeeee eeeeee eeeeeeee.[‌8‌] M eeee eeeeeee ee eeeeee eeeeeee eeee eeeeee eee eeeeeeeee eee eeee ee eeeee eee eeeeeeeeee eee eeeeeeeeeeeee. Meeeee eeeeee eeeeeee eeee eeeeee eeeeeeeeee eeeeeeee eeeeee eeeeeee eeeeeeee eeeeeeee eeeeeeeeeeee ee eeeeeee eeeeeeeeeeeee;[‌88‌‌88‌] eeee ee eeeeeeeeeee eee eeeeee eeeeeeeeeeeeeee, eee eeeeeeeeeee, e eeeee ee eeeeeeee eeeeee ee eeeeeeeeeeee eeeeee eeeeeeeeeeee, eeeeee eeeeee ee eeee e 8:8 eeeeee eeee eeeeee eee eeee eeeeee ee eeeeee eeeeee ee ee eeeeee ee eeee eeeeeeeeeee, eee eeee eeeeeeeeee (Meeee 8).[‌88‌‌88‌] Meeee eeeeeee eeeee eee eeeeeeeeeee ee eeeeeeeeee eee eeeeeee eeeee eeee eee eeeeeeeeeeeee eeeeeeee, eeeeee eee eeeeeee eeeeee eeeeeeeee eee eeeeeeeeeeeeeee eeeeee eeeeeeee.

Meeee 8 Meeeee Meeeeee eeee Meeeeeee Meeeeeee Meeeee eee Meeeeeeeeeeee ee Mee-8-eee ee Meee Meeeeeeeeee ee Meeeeeeeeeeeeee[‌88‌‌88‌]

Meeee Meeeeeee [MM8] Meeeeeeeeeeee Meee (eee) Mee
MeMMe(eMe) 8.8 88 [‌88‌,‌88‌,‌88‌]
MeMMe(eMe) 8.8 88 [‌88‌]
eMe8M(eMe) 8.8 88 [‌88‌,‌88‌]
e-MeMMeeMe 8.8 88 [‌88‌]
e-MeMMe(eMe) 8.8 88 [‌88‌]
e-MeM(MM8MM8MMe)8 8.8 88 [‌88‌]
Me8M[MMe8MM8e-Me] 8.8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

Mee-eee-eeeeeeeeeee (8, M8=M8=Me; M8=M); Meeeeee Meeeeeeee:[‌8‌]

Mee-8-eee (88.88e, 8.8eee) eee eeeeeeeeee eeee e eeeeeeee, eeeee e Meeee eeee eeeeee ee e eeeeeee eeeeee, eeee e 8M eeee ee MM8 ee MMM (88eM, 888eeee) ee 8°M, eeee eeeeeeee eeeee M8. Meeee eee eeeeeeee eee eeeeeeeee, eee eeeeeee eee eeeeeee eee 88eee ee eeeeee eeeeeeee eeeeeeeeeeeee. MMM eee eeeeeee eeeee eeeee-eeeeeeeee eeeeee eeeeeee eee eeeeeee eeee e 88°M eeeee eeee. M8 eee eeee ee eeeeeee eee eeeeee. Mee eeeeeee eee eeeee eeee, eeeeeeee eeeeeeeeeeee eee eeee eeeeeeeeeeee eee eee eeeee eee eeeeeeeeeee eeeeeeeeeeee. Meeeeeeeeeee eeee e 88eM eeeeeee, eeeeeeee ee eee eeee eeeeeeee; eeeee 8888%; ee 8888°M/8Meee. Mee eee-eee-eeeeeeeeeee eeee eee ee eeeeeeeeee, eeeee eee eee-eeeee eeee eee eeeeeee eeeeeeeeeeeee ee eeeee ee eeeeeeee eeeeeeeeeeee. Mee eee eeeeeeeeeee eeeeee eee eeeeee 888°M. Mee eeeeee ee eeeeeeee eeee M8, eeeee eee eeeeeee ee eee-eeeeeeeee.

Meeeeeeeeeeeee [8, M8=(MM8)8Me; M8=M8=M]; Meeeeee Meeeeeeee:[‌8‌]

Mee eeeeee eeeeee (88eeee ee MM8) eeee eee eeeeee eeeee ee 8-[8-(eeeeeeeeeeeee)eeeeee]eeeeeee (8.8eM) eee eeeeeeeee ee MM8Me8 (88eM) eee eee-8-eee (8.88e, 88eeee) eee eeeee eeeeeeee eeee eeeeeee ee eeee eee eeeeeeeeeee ee 8888°M. Meeee 88eee eeeeeeee ee ee, eee 88MMMM eeeeeeee eeeeee eeee e eeeeee ee δ 88 (eeeeeeeeeeeeee) eee e eeeeee ee δ 88 eeeeeeeeeeeeee ee eee eeeeee eeeee. Mee eeeeeee eee eeeeee eeee M8M (8×88eM), 8.8M MeMM (88eM), eee M8M (88eM), eee eeeee (MeMM8). Mee 88MMMM eeeeeeee eee eee eeeeeeee eee eeeeeeee ee eeeeee eeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeeeeeeee eee eeeeeeee; eeeee: 8.88e (88%).