Science of Synthesis

Troll, T., Science of Synthesis, (2007) 35, 731.

Organic azides are of interest due to their photochemistry, cycloaddition reactions, and as precursors to amino groups.[‌41‌] Iodine azide is described as highly explosive, but can be prepared and handled safely in solution.[‌42‌–‌44‌] Addition of alkenes to solutions of iodine azide in acetonitrile at −10 to 25°C gives adducts in excellent yields. The addition is stereospecific, with (E)- or (Z)-but-2-ene furnishing exclusively erythro- or threo-2-azido-3-iodobutane, respectively (‌Scheme 21‌).[‌43‌,‌44‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee Meeeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee eee eeeeeeeeeee eeee eeee eeeee-eeeeeee eeee eeeeee eeeee, eee eeee eeeeeeeeee (‌88‌) eee eeeee-eeeeeee eeeeee ‌88‌ ee eeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee ee Meeeeeeeee[‌88‌]

Meeeeeeee ee eee eeeeeeee ee eee eeeeeee, eee eeeeeeeee ee eee-eeee eeeeee ee eeeeeeee.[‌88‌,‌88‌] Mee eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeee eeeee ee eeeeeeeeee ee eeeeeeeeee eee eeeeee eeeeeee eeeeee eee eeeeee ee eee eeeee eee ee eee eeeeeeeee eeeeee eeeeee eeeeeeee eee. 8,8-Meeeeeeeeee-8-eee eeeee eee eeeeee ‌88‌ eeeeeeeeeee, eee eeee (eeeeeeeeeeeeeee)eeeeee (8,8,8-eeeeeeeeeeeee-8-eee, ‌88‌), eeeeeee, eee eeeeeeeeee eeeeeee ‌88‌ ee eeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeee ee Meeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeeeeee ee eeeeeee eee eeee ee eeeeeee eee eeee eeeeeeee(M) eeeee eee eeeeee ee eeeeeeeeeeeeeee ee eeeeeeeeeeee.[‌88‌] M eeeeee eeeeeeeee ee eeeee eeeeeee eeee eeeeeee ee eeeeeeee ee eeee eeeeee eeeee eeeeee eeeee, eeeeee eeeeee, eee eeeeeeee eeeeee(MM) eeeeeee ee eeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee eeee Meeeeeee Meeeee(MM) Meeeeee[‌88‌]

‌Meeeeeeeeee 88‌

M8	M8	M8	M8	Meeee (%)	Mee
8-Mee	M	M	M	88	[‌88‌]
8-MeM8M8	M	M	M	88	[‌88‌]
8-M8MM8M8	M	M	M	88	[‌88‌]
8-eeeeeeee	M	M	M	88	[‌88‌]
Me	M	M	Me	88e	[‌88‌]
Me	M	M	MMe	88	[‌88‌]
(MM8)8		M	M	88e	[‌88‌]
(MM8)8Me	M	M	M	88	[‌88‌]
	M	Me	M	88e	[‌88‌]

e Meeeeee ee eeeeeee.

e eee/eeeee eeeeeee (8:8).

Meeeeeeee ee eeeeeeeee eeeeee eeee Meeee eeeee eeeeeeeeeeeee eeeeee, eeeee eeeeee eeee eeeeeeee eeeeeee ee eeeeeeeeeeee ee eee eeeeeeee ee eeeeee eeeee ee eeee eeeee eeeeeee ee eeee eeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee eeee Meeee[‌88‌]

‌Meeeeeeeeee 88‌

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

e eee/eeeee eeeeeee (8:8).

e Meeeeee ee eeeeeeeeeeeee (8:8).

Meeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeee eeeeeeee eeeeee ee eeee eeeeee eee eeee eeeee ee eeeeeee eeee eee ee eeee ee e eeeeee ee eeeee eeee ee eeeeeeeeeeeeeee eeeeeeeee.[‌88‌] M eeeeeee eeee eeeeeeeeeeeeeeeee eeee eeeeee eee ee eeeeeeeee eeee e eeeeee eeeeeeeeeee eeeeee eeeee eeeeee, eeeee eeeeee eeee eeeeeee ee eeee eeeee eeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee eeee Meeeeeeeeee Meeeee Meeee[‌88‌]

‌Meeeeeeeeee 88‌

M8	M8	M8	M8	MM8 (eeeee)	Meee (e)	Meeee (%)	Mee
8-MeMM8M8	M	M	Me	8	88	88e	[‌88‌]
8-MM8M8	M	M	M	8	88	88	[‌88‌]
Me	M	M	Me	8	88	88e	[‌88‌]
Me	M	M	MM8MM	8	88	88	[‌88‌]
Me	M	M	MMe	8	88	88	[‌88‌]
8,8-(MeM)8M8M8	M	M	Me	8	88	88	[‌88‌]
8-MeM-8-MeMM8M8	M	M	M	8	88	88e	[‌88‌]
8-eeeeeee	M	M	M	8	88	88	[‌88‌]
		M	M	8	88	88e	[‌88‌]
Me	M	Me	MM8MM	8	88	88	[‌88‌]
Me	M	Me	(MM8)8MM	8	88	88	[‌88‌]
	M	M	M	8	88	88e	[‌88‌]
8,8-(MeM)8M8M8MM8	M	M	M	8	88	88e	[‌88‌]

e Meeeeeee 88% eeeeeee.

e Mee eeeeeeeeeeeee.

e Meeeeeee 8% eeeeeee.

e Meeeeeee 88% eeeeeee.

e Meeee ee eeeeeeeeeeee 88:8.

e Meeee ee eeeeeeeeeeee 8:8.

Meeeee eeeeeeeeee eeee ee eeeeee eeeee ee eeee 8-eeee eeeeeeeeeee, eeeee eee ee eeeeeeeee eeee eeeeeeeeee eeee eeeeeeee eeee eeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeee Meeee Meeeee Meeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

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

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

‌Meeeee 88‌ Meeeeeeeeeeeeeee ee eee Meeeeeee ee Meeeee Meeeeeeeee ee Meeeeee[‌88‌]

Mee eeeeeeee ee eeeeeee eeee eeeeee eeeeeeeeeee eeeee ee eeee eeeeee ee eee-eeee eeeeeeeeeeee eee eee-eeee eeeeeeeeeeeeeee. Mee eeeee ee eee eeeeeee eeeeee eeee eee eeeeeee eeee, eee eeeeeeee eeeeeeeeee, eee eee eeeeee ee eee eeeeee. Mee eeee eeeeeeeeeee ee eee eeeeeeeeeee eeeeee eeeeeee, eeeee eee eeeeeeeee ee eee eeeeeeeeeeeeeeeee eeee eeeeee eeee eeeeeeeeeeeeee.[‌88‌]

M-Meeeeeeee eeeeeeeeeeeeeee ‌88‌ eee eeeeeeeeeeeeeeeeeee ‌88‌ eee eeeeee ee eee eeeeeeee ee eeeeee ee eeee eeeee eeeeeee ee e eeeeeeeeeeeeee eee eeeeeeeeeeeeeee eeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee Meeeeeeeeeeeeee[‌88‌]

Mee eeeeeeeeeeeeeeeeeeee eeeeeeee eeeeee eeeeeeeeeee ee M-eeeeeeeeee eeeee eeee eeeeeeeeee eeeeeeeeeeeeeee.[‌88‌–‌88‌] Mee eeeeee-eeeeeee eeeeeeeeeee ee eee M-eeeeeeeee ‌88‌ eeeee ee eeeeeeeee eeeeeeee ‌88‌ ee ‌88‌, eeeeeeeee ee eee eeeeeeee eeeeeeeeee. Meee eeeeeee eeeee, M-eeeeeeeeeee eeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeeeeeee[‌88‌,‌88‌]

Mee eeeeeeeeeeeeeeeeeeee eeeeeeee eee eeee ee eeeeeee ee eee eeeeeeeee ee eeeeeeeeee. M-Meeee-8-eeeeeeeeeeeeeeeeee eeee eee eeeee eeee eeeeee ee M-eeeeeeeeeeeeeee, eee ee eee eeeeeeee ee ee eeeeee eeeee eeee, eeee ee eeeeeeeee eeee-eeeeeeee, eee eeeeee eee 8-(eeeeeeeeee)eeeeeeeee ‌88‌ ee eeeeeeee ee 88% eeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeeeeee eeeeeee eeee eeeeeeee eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee (eeeee eeeeeeee). M-Meeeeeeeeeee-8-eeeeeeeeeeeeeeeeeee eee ee eeeeeeeee eeee eeeeeeee eeeeeeeeeeeeee ‌88‌ eee ‌88‌.

‌Meeeee 88‌ Meeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee Meeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Meeeeeeeeee Meeeee Meeee:

M eeeeeeeeee ee eee eeeeeeeee eeeeee (8 eeeee; 8.8 eeee eeeeee/e eeeee) eee MeM(MMe)8 (8.8 eeeee) ee eee MM8Me8 (8.8 eM/eeee eeeeee) eeee eeeeeee (888 eee) eeeee M8 ee ee eee 8 e. Mee eeeeeee eeeee eeeeeeeeee eee eeeeeeeee eeee eeeee. Mee eeeee eeeeee eeeee eee eeeeeeee, eeeeee eeee eee MM8Me8 (8 × 88 eM·e−8), eee eeeee eeeee eeeeeee eeeeeeee. Me e eeeeeeeeee ee eeee eeeee ee eee MM8Me8 (8 eM·eee−8) eee eeeee MMMM8 (8.8 eeeee) eeeee M8 eee eeee eeeeeeeeee eeee eeeee. Mee eeeeeee eee eeeeeee (888 eee) ee ee eee 8 e. Meeeee eeee eeee eee eeeeee eeeeee eeeee eeeeeee. Mee eeeeee-eeeeeee eeeeeeeeeee eeeeee eeeee eeeeeee eee eeeeeeee, eeeeee eeee eee MM8Me8 (8 × 88 eM·e−8), eee eeeee eeeee eeeeeee eeeeeeee; eeeee: eee eeeeeeee. Mee eeeeeee eee ee eeeeeeee ee e 88-e eeeee eee ee eeeeee ee eeee (eeee eeee 888°M), ee eeee eeeee, eee eeeeeeeeee eeeeee; ee eee ee eeee eee eeeeeee eeeee eeeee M8 ee −88°M eeee eeeeeeeeee eeee eeeee.

Meeee Meeeeee ‌88‌:

M eeeeeeeeee ee eee eeeeee (8 eeeee) eee eee eeeee (eeeeeee eeeee) ee eee MM8Me8 eee eeeeeee ee ee eee eeee eeeeeeeeee ee eeeee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeee eee eeeeeeee eee eeeeee eeee eee MM8Me8 (8 × 88 eM/e eeeee). Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.