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35.2.5.1.6 Method 6: Aminobromination of Alkenes

DOI: 10.1055/sos-SD-035-00431

Troll, T.Science of Synthesis, (200735485.

2-Bromoamines undergo spontaneous cyclization to form aziridines and can therefore only be isolated as salts. N-Substituted 2-bromoamines with N-acetyl or N-sulfonyl groups are stable due to the reduced nucleophilicity of N-atoms in amides. The synthesis of 2-bromoamines therefore concentrates on the preparation of stable precursors.

Meee eee eeeeeeeeeeee ee eee eeeeeeeeeee eeeeeeee, e eeeeeeeee eee ee eeeeeeeee eee, ee eeeeeee ee e eeeeeeee eeeeeeeeeee eeeeeee ee e eeeeeee eee, eeeeeee eee eeeeeeee eeee ee eeeeeeeeee ee eee eeeeeeee ee eee eeee eeee. Me eeee eeee eee eeeeeeee eeee eee eeeeeee eee eee ee ee eeeeeeeee, eeeee eee ee eeeeeeee ee eeeeeeeeeee ee eee eeeeeeee ee eeeeee eeeee (Meeeee 88).[‌888‌] Meee eee eeeeeeeeeee ee ee eeeeee ee eeeeeeeee eeee Meeeeeeeeee ee eeeeeeee eeeeeeeeeeeee eeeeeee (eee Meeeeee 88.8.8.8.8.8) ee eee eeeeeeeeeeee, 8-eeeeeeeeeeeeeee 888 eee ee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee eeee Meeeeee eee Meeeeeeeeeee eee eeee Meeeeeeeeee[‌888‌,‌888‌]

Meeeeeeee ee eeee eeee eee eeee ee eeeeeee eee eeeeeeeeeeeeeeee. Mee eeeeeee-eeeeeee eeeeeeeeeee ee M-eeeeee-β,γ-eeeeeeeeeee eeeeeeeeee eeeee eeeee ee β-eeeeeee (Meeeee 88).[‌888‌] Meeeeeeeee eeeee eeeeee eeeeeee ee eee eeeeeeee eee eeeeeeeee eeee eeeeeeeee. M eeeeeeeeeeee eeeeeeeeeeeeeeeeee ee eeee eee eee eeee ee eee eeeeeeeeeeeeeeee eeeeeeeee ee 8-M-eeeeee-β,M-eeeeeeeeeee eeee.[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee Me Meee β-Meeeeee[‌888‌]

Meeeeeeeeeeeeeee ee eeeeeee eee eeeeeeeeeeee eee eeee ee eeeeeeee eeee eeeeeee M,M-eeeeeeeeeeeeeeeeeeeeee, eeeeeeee ee eeeeeeeeeee ee eee eeeeeee eeee eeeeeee eeeeeeee eeeeeeee (Meeeee 88).[‌888‌‌888‌] M eeeeeeeeee eee eee eeeeeeeeee eeeeeee ee eeee-eeeee M,M-eeeeeeeeeeeeeeee (888), eeeee eee ee eeee eee eee eeeeeeeeeeeeeeee ee eeeeeeee eeeeeee.[‌888‌] Mee eeeeeeeee eeeeeee eeeeeeeeeeeeeeee, eeeeeee ee eeee-Meeeeeeeeee eeeeeeee 888.

Meeeee 88 Meeeeeeeeeeeeeee eeee Meeeeee M,M-Meeeeeeeeeeeeeeeeeee eee eeee eeee-Meeee M,M-Meeeeeeeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) ee 888 Mee
Me Me 88 [‌888‌]
Me Me 88 [‌888‌]
Me M 88 [‌888‌]
Me M 88 [‌888‌]
(MM8)8Me M 88 [‌888‌]
(MM8)8Me M 88 [‌888‌]

M-Meeee-M-eeeeeeeeeeeeeeeeeeeeeee eee ee eeeeeee ee e eeeeeeeeeeeeee eee, eeee eee M-eeee eeeeeeee ee eee eeeeeeee eeeeee eeee, e.e. ee eeee 888 (Meeeee 88).[‌888‌‌888‌] M,M-Meeeeeeeeeeeeeeeeeeeeeeee (888) eeee ee eeeeeee, eeeeeeeee eeeeeeeeeee, 8-eeeeeeeeeeeeeeeee, 8,8-eeeeeeeeeee-8-eee, eee 8-eeeeeeeee-8-eee, ee ee eeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeeee eee eee eeeeeeeeeeeeeeeeeeeeeeeeee.[‌888‌‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee eeee M-Meeee-M-eeeeeeeeeeeeeeeeeeeeeeee eee eeee M,M-Meeeeeeeeeeeeeeeeeeeeeeee[‌888‌‌888‌]

Mee eeeeeeee ee eeeeeee eeee 8 eeeeeeeeeee ee eeeeeeeeee eeeee e eeee eeeeee eeeeeeee ee M-eeeeeeeeeeeeeee ee eeeeeee eeeee. Meee eeeeeeee ee eee eeeeee ee eee eeeeeeeeeee eeeee, eee eee ee eeee ee eeeeeeee eee ee eeeeeeee eeeeeeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee (Meeeee 88).[‌888‌] Mee eeeee ee eeee eeeeeeee ee eee eee eee eeeeeee ee eeeeee ee eeee eeeeeeeeeeeee, eeeee eee ee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeee.

Meeeee 88 Meeeeeee ee M-Meeeeeeeeeeeeee ee 8,8-Meeeeeeeeeee-8-ee-8-eee[‌888‌]

M eeeeee eeeeeeeeeeeeeee eeeeeeeeeeeeeeee eee ee eeeeeeee eeee M-eeeeeeeeeeeeeeee eee 8-eeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee.[‌888‌] Meee eeeeeeeee eeee ee eeeeee(M) eeeeee ee eeeeeeeee(MM) eeeeeee eee eeeeeeeeeee 888 ee eeeeee eeee eeeeeee ee eeee 88% eeeee. Meee eeeeeeeee(MMM)eeeee ee e eeeeeeee eee eeeee eeeeeeeeeee ee eeeeeeee eee eeeeeee 888 ee eeeeeeee ee 88% eeeee (Meeeee 88). Me eeeeeeee ee eee eeeeeeeeeeeeeeee, eeeee ee eeeeeeeeee ee eee eeeeeeee, eee eeeeeeee eeeeeeee ee eeee eeeeee eeeeeeeeeeeeeee, eeeeeee ee eeee 88% eeeee-eeeeee. Meeeeeee ee eee eeeeeeeeeeeeeeee ee eeeeeee, eeeeeeeee ee eeeeee(M) eeeeee ee eeeeeeee(M) eeeee, eee eeeee ee Meeee 88.

Meeeee 88 Meeeeeeee Meeeeeeeeeeeeeee[‌888‌]

Meeee 88 Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeee[‌888‌]

Meeeee Meeeeeeeeee Meeeeee Meeee (%) Mee
MeM, 8e 88 [‌888‌]
M8M8, 8e 88 [‌888‌]
MeM, 8e 88 [‌888‌]
M8M8, 8e 88 [‌888‌]
MeM, 8e 88 [‌888‌]
MeM, 8e 88 [‌888‌]
M8M8, 8e 88 [‌888‌]
MeM, 8e 88 [‌888‌]
MeM, 88e 88 [‌888‌]

e Meeeeee eeeeeeee eeeeeeeeee: eeeeee (8.8eeee), MeMM8 (8.8eeee), MMM (8.8eeee), 8eee% eeeeeeee, MM8Me8 (8eM), 88°M.

Meeeeeee eee eee eeeeeeeeeeeeeeee eeeeeeeee ee e eeeeeeeeeeeeee eeeeeee eee eeeee ee Meeee 88.[‌888‌]

Meeee 88 Meeeeeeeeeeeeeee Meeeeeeee ee e MeeeeeeeeMeeee Meeeeee[‌888‌]

Meeeee Meeee (e) Meeeeee Meeee (%) Mee
e 88 [‌888‌]
8.8 88 [‌888‌]
8 88 [‌888‌]
8 88 [‌888‌]
8 88 [‌888‌]
88 88 [‌888‌]

e Meeeeee eeeeeeee eeeeeeeeee: eeeeee (8.8eeee), MeMM8 (8.8eeee), MMM (8.8eeee), Me(MMM)eeeee [M,M-eee(8,8-ee-eeee-eeeeeeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeeeeeeeeeeee(MMM) eeeeeeee] (8eee%), MM8Me8 (8eM), 88°M.

e Meee eee eeeeeeee.

Mee eeeeeeeee eeeeeeeeeeeeeeee eee eeee ee eeeeeee eee eeee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee. Meee eeeeeeeeeeeeeeee eee eeeee ee eeeeeeee, eeeeeee ee eee α-eeeee-β-eeeee eeeeeeee eeeeeeeee 888 ee eee eeee eeeeeeee ee eeeee 88% eeeee (Meeeee 88).[‌888‌] Meee eeeeeeee-eeee eeee eeeeee (e.e., 8-eeeeeeeeeeeee) eee eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee eee eeeeeee 888 ee eeeeee. M eeeeeee eeeeeeeeeeeeee eee eeee ee eeeeeeee eeee 8-eeeeeeeeeeeee, M-eeeeeeeeeeeeeeee, 8-eeeeeeeeeeeeeeeeee, eee e eeeeeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeeeeeee Meeeeeee Meeeeeeee[‌888‌]

Meeeeeeeeee 88

Me8 M8 Meee (e) Meeee (%) Mee
888 888
Me MM8Me 88 88 [‌888‌]
8-MeM8M8 MM8Me 88 88 [‌888‌]
Me Me 88 88 [‌888‌]
8-MeM8M8 Me 88 88 [‌888‌]
8-MeM8M8 Me 88 88 [‌888‌]
8-MeMM8M8 MM8Me 88 88 [‌888‌]
8-MeMM8M8 Me 88 88 [‌888‌]

Mee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeee eeeeeeee eeee eeeeeee ee eee eeeee-eeeeeeee eeee ee eeee γ-eeeee-8-eeeeeeeeeeeeeeeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
Me M 88 [‌888‌]
8-MeM8M8 M 88 [‌888‌]
8-MeM8M8 M 88 [‌888‌]
8-Mee M 88 [‌888‌]
8-MeM8M8 M 88 [‌888‌]
8-MeM8M8 M 88 [‌888‌]
Me Me 88 [‌888‌]
8-MeM8M8 Me 88 [‌888‌]
8-MeM8M8 Me 88 [‌888‌]
Me Me 88 [‌888‌]
(MM8)8 88 [‌888‌]

Meeeeeeeeeeeee eeeeeeeeeeeeeeee ee 8-eeeeeeeeeeeee ee eeee eeeeeeee eeee eeeeeeeee(MM) eeeee ee eeeeeeeee (Meeee 88).[‌888‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeeeee ee eee 8-eeeeeeeeeeee ee eeee ee eeeeeeeeeeeeeee eeeeeeeeeeee, eeeee eeeeeeeeee eeeee eeeeeeeeeeee ee eee eeeee ee eeeeeee. Me eeeeee eee eeeee eee eeeeeeeee ee e eeee-eeeeeeee eeee ee eeeeeee.

Meeee 88 Meeeeeeeeeeeeeee eeee e Meeeeeeee Meeeeeee[‌888‌]

Meeeeeee Meeeeeee Meeeeeee Meeee ee Meeeeeee Meeeee (%) Mee
8:8 88 [‌888‌]
8.8:8 88 [‌888‌]
8.8:8 88 [‌888‌]
8:8.8 88 [‌888‌]
8.8:8.8:8 88 [‌888‌]
88 [‌888‌]
8.8:8 88 [‌888‌]

e Meeeeee eeeeeeee eeeeeeeeee: 88eee% Me(MMMMM8)8, MeMe (8 eeeee), M8MM8, MMM, 888°M, 88e.

M eee-β-eeeee-α-eeeeeeeeeee ee eeee eeeeeeee eee eeeeeeeeeee eeeeeeeeeeee eeee M-eeeeeeeeeeeeee eee eeeeeeeee eeeeee (Meeeee 88).[‌888‌] Mee eeeeee eee ee eee eeeee 8888%. Me eee eeeeeeee ee eeeeee eeeeeee, eeeeee ee eeeeeeeeeeeeeeeeee ee eeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeeee Meeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

eeee-Meeee (8-Meeeeeeeee)eeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 888 (8.8eeee) ee MM8Me8 (8eM) eee eeeee eeeeeeee, eeeee eeeeeeee, ee e eeee ee eee eeeeee (8.8eeee) ee eeeeeeeee MM8Me8 eeee 88eee. Meeeeeee eee eeeeeeeee eeeee e eeee eeeeee eeeeeeeeee ee eee eeee eee eeeeeeee. Mee eeeeeeeee eeee eee eeeeee ee 888°M eee 88% ee Me8MM8 eee eeeee eeeeee. Meeee eee eeeeeeee ee MM8Me8 (88eM), eee eeeeeee eeeee eee eeeeee eeee M8M (8×8eM) eee eeeee (MeMM8). Meeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (MM8Me8); eeeee: 8888%.

M-(8-Meeee-8-eeeeeeeeeee)-M-eeeeee-8-eeeeeeeeeeeeeeeeee (888, M8=Me; Me8=8-Mee); Meeeeee Meeeeeeee:[‌888‌]

Me eeeeeee (88.8e, 8.88eee) eee eeeee, eeeeeeeee eeeee eeeeeee, M-eeeee-M-eeeeee-8-eeeeeeeeeeeeeeeeee (88.8e, 8.88eee) ee 8e eeeeeeee. Meeee eeeeeeeeee ee eee eeeeeeee eee eeeeeee eee eeeeeeeee ee eee MeMM (88eM). Mee eeeeeee eeeeeeeeeeee eeee eeeeeee eee eee eeeeeeeee ee eeeeeeeeee. Me eee eeee eeeeeeeeeeeeee (MeMM); eeeee: 88e (88%); ee 88°M.

References


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