Science of Synthesis

Bräse, S.; Lesch, B.; Zimmermann, V., Science of Synthesis, (2010) 41, 585.

Alkenes react with a number of reagents resulting in formation of β-haloalkyl azides. This is known as the Hassner reaction.[‌11‌,‌130‌–‌134‌]

Meeeee eeeee (MM8) eeeeee eeee eeeeeee eee eee eeeeee eeeeeeee eee ee e eeeeeeeeeeeeee eee, eeeeeee eee eeeeee eee eee eeeee eeeeeeeeeeeee eee eeeeeeeeee eeee ee eeee eeeee. Mee eeeeeee, eee eeeeeeee ee eeeeee eeeee ee eeeeeeeeeee eeeeee eeeeeeeeeee eeeee-8-eeeee-8-eeeeeeeeeeeeeee (‌888‌) (‌Meeeee 88‌).[‌88‌] Meeee eeeeeeeeeeee, eeee ee eee eeee-eeeee eeeee, eeeeeeeee eee eeeeeeeeeeeeeeee ee eee eeeee eeeeeeee, eee eeeeeeeeee eeeeeee, eeee ee eeeeeeee ee e eeeeee eeeee, eeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeeeeee Meeeeeee ee Meeeee Meeee ee Meeeeeeeeee[‌88‌]

‌Meeeee 88‌ Meeeee Meeeee Meeeeeeeee Meeeeee Meeeee Meeeeeee ee Meeeee Meeee ee Meeeeee[‌88‌]

Mee eeeeee eeeeeeeee eeeeee eeeee ee eeeeeeee eeee eeeeee eeeeeeeeeeee eee eeeeee eeeee ee eeeeeeee eee eeee ee eeee eeeeeee eeeeeeeeeeee.[‌888‌,‌888‌] Meeee eeeeee eeeee, eeeeeee eeeee, eee eeeeeeee eeeee eee eeeeeee ee eeeeeeee eeee eeeeeee eee eeee eeeee eee eeeeeee eeeeeeee, eee eeeeeeeee ee eeeeeeeeeeeeeeee eeeeeee eeeeeee eeee eee eeeeeeee ee eee eeeeeee (‌Meeeee 88‌).[‌888‌,‌888‌] Meeee eeeeeeee eeee ee eeeeeeeeeeee eeeee ee eeeee eeeeeee, eee e eeeeeeee eee (e.e., ‌888‌), eeeeeee eeeeeeee eeeeeeee eeee ee eeeeeee eeeee e eeeeeee eeeeeee eee ee eeeeeeeeeeee eeeee eeeeeee (e.e., ‌888‌). Meeeee eeeee eeeeeee eee eeeee eeeeeee eee eeeeeeee eeeee eeeeeee eee eeeeeee eeeeeee. Meeeeeee eeeeeee eeeee ee eeeeeeee eeee eeeeeeeeeeee eeeeeeee, eeeeeeee ee eeeeeeeeeeee eee eeeeeeee. Meeeeeeee, eeeeee eeeee eee eeeeeeee eeeee eeee eeeeeeeeeeeee eeeeeeee eeee eeee ee eeeeeeee eeeeeeee eee eeeeeee eeee ee eeeeeeee ee eee eeeeeee’e eeeeee.

‌Meeeee 88‌ Meeeeee Meeeeee Meeeee Meeeeeee ee Meeeeee Meeee ee Meeeeee[‌88‌]

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

‌Meeeee 88‌ Meeeeeeeeeeee Meeeeeee ee Meeeee Meeee ee Meeeeeee-8-eeeee[‌888‌]

M eeeeee eee eeeeeeeee eeeeeeeeeeeeeee eeeeee ee eee eeeeeeee ee eeeeeee ‌888‌ eeee eee(eeeeeeee)eeeeee(M) eeeeeeeeeeeeeeeee (‌888‌) eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeeeeeee eeeee eeeeeeeeeee eeee-eeeeeeee ‌888‌; eeeeeee, eee eeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeeeeee eee ee eeeeeeeeee ee eeeeeeeeeee. Mee eeeeeeee ee e eeeeee eeeee eeeeeeee eeeeeee eee eeeee eeeee ee eee eeeeeeee eeeeeeee (ee ee eee eeeeeeeee ee eeeee ‌888‌ eeee eeeeee), eeeee eeeee eeeeeeeeeeee eeee ee eee eeee-eeeee eeeee eeee ee eeee-Meeeeeeeeee eeeeeeee. Meeeeeeeeeeeee eeeeeee eee eeee eeeeeeee eeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeeee eeee Mee(eeeeeeee)eeeeee(M) Meeeeeeeeeeeeeeee, Meeeeeeeeeeeeeeeeeee eee Meeee Meeeeeeeeee–Meeeeee Meeee Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeee ee eee 8:8 eeeeeeeeeeeee eeeeeee; eeeeeeee ee M8 eee M eeeeeeee ee eeeee eeeeee.

e Meeee ee eee 8:8 eeeeeeeeeeeee eeeeeee; eeeeeeee ee M8 eee M eeeeeeee ee eeeee eeeeee.

e MMM eeee eeeeeee ee MM8•MMe8.

e Mee(eeeeeeee)eeeeee(M) eeeeeeeeeeeeeeeeeeeeeeeee eeee eeeeeee ee eee eeeeeeeeeeeeeeeee.

Meeeeee eeeeee eee eeeeeeeeeeeeee 8,8-eeeeeeeeeeeee ee eeeeeee ee eeeeeeee eeee Meeee (eeeeeeeee eeeeeeee eeeeeeeeee), eeeeee eeeee, eee eeeeeeeee eeeeee ee eee eeeeeeee ee eee eeeeeee (‌Meeeee 88‌).[‌888‌] Meeeeee ee eeeeeeeee eee eee eeeeeeee. Me eeeeeeeeee, eee eeeeeeeeeeeeeeee ee eeeeeeee ee eee eeeeeee eeeeeeee eeeeeee eeeeeeee eeee-Meeeeeeeeee eeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeeee eeee Meeeeeeee Meeeee, Meeeee Meeee, Meeee, eee Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

M8	M8	M8	Meeee (%)	Mee
M	(MM8)8		88e	[‌888‌]
Me	M	M	88	[‌888‌]
	Me	M	88e	[‌888‌]
(MM8)8Me	M	M	88	[‌888‌]
8-MM8M8	M	M	88	[‌888‌]
8-e-MeM8M8	M	M	88	[‌888‌]
(MM8)8MM8Me	M	M	88	[‌888‌]

e Meeeeeee ee 8:8 eeeee/eee eeeeeee.

e Meeeeeee ee e 8:8 eeeeeeee eeeeeee.

Meeeeee ‌888‌ eee ee 8,8-eeeeeeeeeeeee ee M-eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeee eeeeeeeeeeeeeeeeeeeeeeeeee eeee eeeeeeee ee eeee eeeeee. Meee eeeeeee eee eeeeeeee eeee eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeee eeee-eeeeeeee ‌888‌. Meeeeee eeeeeeee, eee eeeeeeee eeee eeeeeeeee eeeeeeeeeeee eee eeeeeeee ee 8,8-eeeeeeeeeeeee eee eeeeee ee eeeeeeeeeee eeeeeee. Meeeeeeeeeeeee ee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee eeeeeeee eeeeee eeeeeeeeeeee eee eeeeeeeee eeeeeeee eeeee.

‌Meeeee 88‌ Meeeeeeeeeeeee ee Meeeeee eeee Meeeeeeeeeeeeeeeeeee/M-Meeeeeeeeeeeeeee eee Meee(MM) Meeeeeeeeeeeeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

M8	M8	M8	Meee (°M)	Meee (e)	Meeee (%)	Mee
Me	M	M	8	8.88	88	[‌888‌]
		M	8	8.88	88	[‌888‌]
(MM8)8		M	8	8.88	88	[‌888‌]
8-MeMM8M8	M	Me	8	8.88	88	[‌888‌]
Me	M	Me	88	88	88	[‌888‌]
Me	M	MM8Me	88	88	88	[‌888‌]
8-MeMM8M8	M	MM8Me	88	88	88	[‌888‌]

Meeeee α,β-eeeeeeeeeee eeeeeeeeee eeee eeeeeeeeeee ‌888‌ eee ee eeeeeeeeeeeee ee M-eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeee eeee eeee eeeeee eee eeee eeeee- eee eeeeeeeeeeeeeeeee (‌Meeeee 88‌). Meee eee eeeeeeeee ee (8M)-eeeeeee eeeeee, eeeeeeeeeeeeee eeeeee ee 88:88 ee 88:88 eee eeeeeeee, eee eeee (M,M)-8,8-eeeeeeeeeeeeeeeeeee ee eeee, eeeeeeeeeeeeee eeeeee ee 88:88 ee >88:8 eee eeeeeeee.[‌888‌] Mee eeeeee eeeeeeeee eee ee eeeeeee ee eeeeeeee eee eeeeeee eeeeeeeeeeeeeee eeeeeeee ee ‌888‌ eeee eeeeeee eeeeeeeee eee eeeeeeee eeeeeeee ee eeee eee eeeeeeeeeeeee α-eeeee-β-eeeee eeeeeeee eeeee ‌888‌ eeeeeeeeeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeee ee Meeeee α,β-Meeeeeeeeee Meeeeeeeee Meee Meeeeeeeeee eeee Meeeeeeeeeeeeeeeeeee/M-Meeeeeeeeeeeeeee eee Meeeeeeee(MMM) Meeeeeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeeee ee eeeeeee ee eeee ee eee eeeee eeee ee eeeeeee eeeee eeeeee {eee Meeeeee ee Meeeeeeee, Mee. 88 [Mee—M Meeeeeeee (M = M, Me, Me, M, M) (Meeeeee ‌88.8.88.8.8‌88.8.88.8.8)]}.

Meeeeeeeeeee Meeeeeeee

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

MMMMMMM: Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

MMMM8 (8.88 e, 8.8 eeee) eee eeeee ee e eeee ee eee(eeeeeeee)eeeeee(M) eeeeeeeeeeeeeeeee (‌888‌; 8.88 e, 8 eeee) ee MM8Me8 (88 eM) ee 8°M eeeee e M8 eeeeeeeeee. Me eee eeeeeeeee eeee ee 8°M eee eeeee eeeeeeee MM8•MMe8 (8.88 e, 8 eeee). 8M-Meeeee (8.88 e, 8 eeee) eee eeeee ee eeee eee eee eeeeeee eee eeeeeee ee 8°M eee 8 e. Mee eeeeeee eee eeeeeeee eeee 8% ee Me8M8M8•8M8M (88 eM) eee eeeeeeeee eeee MM8Me8 (8×88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee M8M (8×88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8) ee eeee eee eeeeeee ee eeeee eeeee; eeeee: 8.88 e (88%).

Meeee Meeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

Me e eeeeeeeeee ee eeeeee ‌888‌ (8.88 eeee) eee 8-Å eeeeeeeee eeeeee (8.888 e) ee eee MM8Me8 (8.8 eM) eee eeeee eeeee eeeee eeee eeeeeeee Me(MMe)8 (8 ee, 8.888 eeee). Me 8°M (ee eeeee eeeeee ee eee eeee ee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee), MMMM8 (8.8 eM, 8.88 eeee) eee MMM (8.888 e, 8.88 eeee) eeee eeeeeeeeeeee eeeee. Mee eeeeeeee eee eeeeeeeee ee MMM. Meee eeeeeeeeee ee eee eeeeeeee (8.88–88 e), eee eeeeeee eee eeeeeeee eeee ee MeMMM8 eee eeeeeeeee eeee MM8Me8 (8×88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe); eeeee: 88–88%.

References