Science of Synthesis

Zaidlewicz, M.; Krzeminski, M., Science of Synthesis, (2005) 6, 1146.

Trialkylboranes react with monosubstituted ammonia derivatives containing a good leaving group to give primary amines (‌Scheme 96‌).[‌330‌–‌335‌] Hydroxylamine-O-sulfonic acid is the reagent of choice,[‌329‌] but chloramines,[‌330‌–‌332‌] or mesitylsulfonylhydroxylamine can also be used.[‌333‌]

‌Meeeee 88‌ Meeeeee Meeeee eeee Meeeeeeeeeeeeee ee Meeeeeeee eeee Meeeeeeeeeeee-M-eeeeeeee Meee[‌888‌–‌888‌]

M eeeeeeee eeeeeeeee eeeeeeeee eeeeeeeeee eeeeeeeee ee eeee eee eeee eeeeeeeee eee eee eeeee eeeeeeeee ee 88M-eeeeeee eeeeeee eeeeee.[‌888‌,‌888‌] Meeeeeeee eeee ee eeeeeee eeeeeee eeeee eeeeeeee eeeeee ee eeeeeee eeeeee.[‌888‌,‌888‌] Mee eee ee eeeeeeeeee-M, [M-(eeeee)] eeeeeeeeeeeeee (MeM=MMe), M-eeeeee-M-eeeeee eeeeeeeeee, eee eeeeeee eee eeeeeeeee eeee-eeeee-M-eeeeeeeeeeeeeeeeee, eeeee ee M-eeeeeeeee eeeeee (eeeeeeeeeeee),[‌888‌] M-eeeeeeeeeeeeeeeeeee,[‌888‌] M-eeeeeeeeeeeeeee,[‌888‌]eee M-eeee-eeeeeeeeeeeeee eeeeeeeeeee,[‌888‌] eeeeeeeeeeee. Me eeeee eeeeeeeee eeeeeeeee eee ee eee eeeee eeeeee eeeeee ee eee eeeee eeee eeeeeeee eee eeeeeee eeeee ee 88% ee 88% eeee eeeeeeeeeee eeeeeeeeeeeeeee. M eeeeeeeeeee eeeeeeeeeee ee eeeee (88–88%) ee eeeeeeee ee eeeee eeeeeeeeeeeeeeeeeeee, eeeee eeeee eeeeee eeeeeee ee eeeeeeeeee ee eee eeeeee eeeee.[‌888‌] Mee eeeeeeeeeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeeeeeeee ee eeeeeee eeee eeeeeeeeeeeeee eeeeeeeee ee eeee eeee eeeeeee eeeeeeeeeeeeeeeeeee.[‌888‌,‌888‌] Mee eeee eeeeeeeeee eeeeeeeeeeee ee eee eee ee eeeeeeeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeee ee eeee eeeee eeeeee eee eee eeeeeeeee. Meee, eeeeeeeeeeeeeeeeeeee, eeeeeee eeeeeeeee ee eeeeeeeeeeeee ee eeeeeee eeee eeeeeeeeeeeeeeee, eee eeeeeee eeee eeeeeeeeeeeeeeeee ee eeee eeeeeeeeeeeeeeeeeeee, eeeee eee eeeeeee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeee ee eeeeeeeee eeeeee ee eee eeeeeeee eeee eeeeeeeeeeeee-M-eeeeeeee eeee. Meeeeeeee eeee eeeeeeeeeeeeee eeee eeee eeeeeeee eeeee (+)- eee (−)-α-eeeeee, (+)-8- eee (+)-eeeeee, (+)-eeeeeeeeeee, eee (−)-β-eeeeee ee eee eeeeeee eeeeeeee eeeeeeeee.[‌888‌,‌888‌] Me eeeeeee, eeeeeeeeeeeeeeeeeeee [(8M,8M,8M,8M)-8,8,8-eeeeeeeeeeeeeeee[8.8.8]eeeeee-8-eeeee] (‌88‌), ee eeeeeeee eeee α-eeeeee (‌Meeeee 88‌).[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeeeeeee eeee α-Meeeee ee Meeeeeeeeeeee–Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeeee

(8M,8M,8M,8M)-8,8,8-Meeeeeeeeeeeeeee[8.8.8]eeeeee-8-eeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌,‌888‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

8 M Me8Me (88 eeee eeeeeeeeee ee eee eeeeeee) ee eeeeee (88 eM) eee eeeee eeeeeeee ee e eeeeeee eeee ee M-eeeeeeeeeeeeeeeeeeeeeeeeeeeee[‌888‌] (88.88 e, 88 eeee) ee eeeeeee (88 eM) ee 8°M. Meee eeeeeeee ee Me8Me, eee eeeeeeeee eeeeeee eeeeee eeee eeeeee eee e eeeee eeeeeee eeee eeeeeeeeeeee eee ee eee eeee. Mee eeeeeee eee eeeeee ee ee eee eeeeeee ee eeee eee 8.8 e. Mee 88M MMM eeeeeeee ee ee eeeeeee ee eee eeeeeeeeeee eeeeee eee eeeee eeeeeeeeeeeee ee M-eeeeeeeeeeeeeeeeeeeeeeeeeeeee (δ 88) eee eee eeeeeeeee ee M-eeeeeeeeeeeeeeeee(eeeeee)eeeeee (δ 88). Mee eeeeeeeeeee eee eeeeeeeee ee eeeee ee e eeeeeee, eeeeee eeee ee MM8Me (88 eM), eeeee M8, eee eeeee (MeMM8). Meeeeee ee eee eeeeeeeee eeeeeeeee eeeeeeeeeeeeeeeee(eeeeee)eeeeee; eeeee: 88.88 e (88%).

Meeeeeeeeeeee-M-eeeeeeee eeee (88.88 e, 888.8 eeee, 8.8 eeeee) eee eeeee eeeeee eeeee e eeeee eeeeeeee eeee ee ee ee eee eeeeeee eeeeeeee eeeeeeeeeeeeeeeee(eeeeee)eeeeee ee MMM (88 eM). Mee eeeeeeeeeee ee eee eeeeeeee eee eeeeeeeeee ee eee eeee eeeeeeee ee eee eeee. Mee eeeeeee eee eeeeeee ee ee eeeee eee eeeeeee eeeeee eeeeee e eeeee eeee (8 e). Meee eee eeeeeeee eee eeeeeeee (88M MMM), eee eeeeeee eee eeeeeee eeeee eeeeee (88 Meee). Mee eeeeeeee eeeeeee eeee eee eeeeeee eeee MeMM (8 eM), eeeee MMe (88 eM), M8M (88 eM), eee Me8M (88 eM). Mee eeeeeee eee eeeeeee ee ee eee 8.8 e, eee eeeeee eeeeeee eeeee eee eeeeeeeee, eeeeee ee 8°M, eee Me8M (88 eM) eee eeeee. Me eee eeee eeee eeeeeeee eeeeeeee ee eeeeee eeeee MeMM eee eeeeeeee. Mee Me8M eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeee eeeeeeee, eeeee (MeMM8), eeeeeeeeeeee, eee eeeeeeeee ee eeeeeee eee eeeeeee; eeeee: 88.88 e (88%); ee 88–88°M/88 Meee; [α]M88 (eeeeeeeeeeeee eeee) −88.88 (e 8, MeMM); ee 888°M. MM eeeeeeee ee eee [8-(eeeeeeeeeeeeeee)-8-eeeeee]eeeeee eeeeeeeee ee eee eeeeeee eeeee e Meeeeeeeee eeeee eeeeeeeee eeeeee (88 e, 888°M, eeeeeeeeee) eeeeee ee ee ee eeeeeeeee eeee (≥88% ee).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8e, 888.