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35.2.5.1.3.2 Variation 2: Generation of Electrophilic Bromine by In Situ Oxidation of Bromide

DOI: 10.1055/sos-SD-035-00431

Troll, T.Science of Synthesis, (200735465.

1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (88, Selectfluor, Scheme 35) oxidizes bromide ions and generates electrophilic bromine, which can be used in situ for bromination and hydroxybromination of alkenes (Table 9).[‌275‌] The bromination is stereoselective: only trans addition and formation of (R,R/S,S)-dibromides is observed.

Meeeee 88 Meeeeeeee ee Meeeeeeeeee[‌888‌]

Meeee 8 Meeeeeeeeee Meeeeeee ee Meeeeeeeeee[‌888‌]

Meeeeeeee Meeeeee Meeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88e [‌888‌]

e Me e 88:88 eeeee.

Meeeee(MM) eeeeeee eeeeeee eee eeeeeeeeeee ee eeeeeee ee eeeeeeeeeeee, eeeee eeee eeee ee e eeeeeee eee ee e eeeeee eeeee eeeeee eee eee eeeeee eee. Me eee eeeeeeee ee eeeeeee, eeeeeeeeee 88 eee eeeeeeee ee eeee eeeeee eee ee eeee eeeee eeeeeeeeeee (Meeeee 88).[‌888‌] Meeeeee eeeeeeeeee eee ee eeeeeeeeee eeee eeeeee(MM) eeeeeee ee eeeeee eeeeeeeeeeee eeeee.[‌888‌] Meeeeeeee eeeeeeeeeee eee eeee ee eeeeeee eee eeeee eeeeeeee eeeeee(MM) eeeeeee eee eeeeeeeee eeeeeee ee eeee eeeeeeeeee 88.[‌888‌]

Meeeee 88 Meeeeeeeeee Meeee Meeeee(MM) Meeeeee eee Meeee Meeeeeee Meeeee(MM) Meeeeee eee Meeeeeeee Meeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

Meeeee Meeeeee Meeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

M eeeeeee ee eeeeeeeeeeeeee eee ee eeeeeeee eeee eee eeeeee ee eeeeee eeeeeeeeeeeee eeee eeeeeeeeeee eeee eee eeeeeee 88% eeeeeeee eeeeeeee ee 88% eeee-eeeee eeeeeeeeeeeee (Meeeee 88).[‌888‌] Meeeee eeeeeee eeee eeeee-eeeeeee. Meeeeeeeeeeee eeeeeee eee eeee ee eeeeeeee ee eeee eeee eeeeee eeeeeee eee eeeeeeee eeeeeeee ee eeeee eeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeee eeee Meeeeeeeeee Meee eee Meeeeeee Meeeeeee[‌888‌]

Meeeeeeeeee 88

Meeeee Meeeeee Meeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

Meeeeeee eeeeeeeeee, eeeeeeee eeeeeeeeee, eee eeeeeee eeee eeeeee eeeeeeeeeee eee ee eeee ee eeeeeeeee eee eee eeeeeeeeeee ee eeeeeee ee e eee-eeeee eeeeee ee eeeeeeeeeeeeeee eee eeeee eeeeeeeeee e eeeeeeeee eeeeee, eeeeee eeeeeee, eee eeeeeeee eeeeeeee.[‌888‌]

Meeeeeee ee Meeee (8MMMM8MMMM8M8MM8) eee eeeeee eeeeeee eeeeee eeeeeee, eeeee eee ee eeeee ee eeee ee eeeeeee ee eeee eeeeee. Mee eeeeeeee eeee α,β-eeeeeeeeeee eeeeeeeee eee eeeeeee ee eeeeeeee ee eeeeeeeeeee ee eeeeeeee eeeeeee ee eeee eee α-eeeee eeeee eeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeee eeee MeeeeMeeeee Meeeeee[‌888‌]

Meeeeeeeeee 88

Meeeee Meeeeeeeee Meeeeee Meeee (%) Mee
8°M 88 [‌888‌]
8°M 88 [‌888‌]

Meeeeeeeeee 88M

Meeeee Meeeeeeeee Meeeeee Meeee (%) Mee
MMe8, M8M, 8°M 88 [‌888‌]
MMe8, M8M, 8°M 88 [‌888‌]
MMe8, M8M, 8°M 88 [‌888‌]
MMe8, M8M, 8°M 88 [‌888‌]
88°M 88 [‌888‌]

M eeee eeeeeeeee eeeeeeeeeee ee eeeeeee eee eeeeeeeeeeee eee ee eeeeeee eee eeee eeee(MM) eeeeeee eee eeee(MM) eeeeeee, ee eeee eeeeee (Meeeee 88).[‌888‌] Meeeeee eee eeee ee eeeeeee ee eee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeee eeee Meee(MM) Meeeeee eee Meee(MM) Meeeeee[‌888‌]

Meeeeeeeeee 88

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

Meeeee eeeeeeeee eeeeeeee eeeeeee eeeeeee eeeee eeee eeeeeeeeee ee eeee eeeeeeeeeeeee eeeeeee, eeeee eee eee ee e eeeeeee ee eeeeeee ee eeee eeeeee. Meeeeeeee eeeeeeeee ee eeeeeeeeee ee eeeeeeee ee eeeeee eeee ee eee eeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeee eeee Meeeee Meeeeeeee eee Meeeeee Meeeeee[‌888‌]

Meeeeeeeeee 88

Me8 M8 Meeee (%) Mee
Me M 88 [‌888‌]
8-Mee M 88 [‌888‌]
8-MeMM8M8 M 88 [‌888‌]
8-MeM8M8 M 88 [‌888‌]
8-MeM8M8 M 88 [‌888‌]
Me MM8MM 88 [‌888‌]
Me MM8Me 88 [‌888‌]
8-Mee MM8Me 88 [‌888‌]
MMMM8 M 88 [‌888‌]
MMMMe8 M 88 [‌888‌]
(MM8)8 88 [‌888‌]

M eeeeeee ee (eeeeeeeeeeeee)eeeeeee eee eeeeeee eeeeeee eeeeeeeee eeeeeeeeeeeee eeeeeee ee eeeeeee eeeeeeee eeee ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee. Mee eeeeee eeee ee eeeee eeeeee eeeee eee eeeeeee eeeeee eee ee eeeeeeeeee ee 8888% eeeee.[‌888‌] Meeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeee eee eeee ee eeee eee eee eeeeeeeeeee ee eeeeeee ee eeeeeeeeeeeeeee ee 8°M, ee eeee eeeeee.[‌888‌] Meeeeeee eeeeeeee-8-eee-8,8-eeeeeeeeeeeee eee ee eeeeeeeeee ee 88% eeeee ee eeeeeeeeeeee ee e eeeeeee ee eeeeeeeeeeee, eeeee, eee eeeeeeeee eeeeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeee-eeeeeeee eeeee eeee e eeeeee eeeeeeeee eeee eeeeee MeMM (88888eM), eee eeeeee (8.888.8eee), eee MeMe8 (8.88.8eee). Mee eeeeeeee eee eeeeeee eee ee ee eee 8eee ee eeeeeee eeeee ee ee 8888°M eee 8.88e. Mee eee ee eee eeeeeeee eee eeeeeeeee ee eee eeeeeeeeeeeee ee MeMe, eeeee eee eeeeeeeee ee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeee eeee eee eeeeee eeee eeeeeee, eee eeeeeeee eee eeeee ee M8M (888888eM), eee eee eeeeeee eee eeeeeeeee eeee eeeeeee (8×88888eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 8888%.

8,8-Meeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌,‌888‌]

Me e eeee ee eee eeeeee (88eeee) ee MM8Me8 (8888eM) eee eeeee MMe (8.888.8eeee) eee e eeee ee MMM (8.888.8eeee) ee M8M (8888eM), eee eee eeeeeee eee eeeeeee ee ee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee eeeee, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eee eee eeeeeee eee eeeeeeeeeeeeee ee eeeeeeeee; eeeee: 8888%.

Meeeee eeeeeee-8,8-Meeeeee-8-eeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee eeeeee eeeeeeeee (888ee, 88eeee) ee MMe8 (88eM) (MMMMMMM: eeeee) eeee ee ee, e eeeeeee ee 88% M8M8 (8.8eM, 88eeee) eee MMe (8.88eM, 88eeee) (eeeee ee 8°M) eee eeeee eeee 88eee. Meeee eeeeeeeeee ee eee eeeeeeee (8e, ee MMM), eee eeeeeee eeeee eee eeeeeeeee eee eeeeee eeee M8M eee eeeee, eee eeeee (Me8MM8). Meeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eee ee eee eeeeeee; eeeee: 888ee (88%).

8-Meee-8,8-eeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeeeeee ee eee eeeeee (88eeee) eee MeMe (88eeee) ee MeMM (88eM), eee eeeee MeMM8 (8.8eeee) ee eeeeeeee. Mee eeeeeeee eee eeeeeeeee ee MMM; eeeee eeeeeeeeee, eee eeeeeee eee eeeeeee eeee M8M eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeee eeeee eee eeeeee eeee eeeeee eeeee ee MeMMM8, Me8MM8, eee eeeee, eee eeeee (Me8MM8). Meeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8) ee eeeeee eee eeee eeeeeee; eeeee: >88%.

References


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