Science of Synthesis

Jung, N.; Bräse, S., Science of Synthesis, (2010) 41, 642.

The synthesis of (E)-tetraz-2-enes via oxidative dimerization of hydrazines is the most commonly used synthetic procedure. There are many variations of these oxidative dimerizations and a large number of oxidizing agents can be used (‌Scheme 2‌).[‌8‌–‌34‌] The most popular reagents are mercury(II) oxide, potassium permanganate, and bromine. A summary of these experimental procedures, and various others, can be found in Houben–Weyl, Vol. E 16a/2, p 1227ff. Some procedures allow quantitative formation of tetraz-2-enes.

Meeeeee, eeeeeeeee eeeeeeeeeeee eeeeee ee eeee ee eeeeeeeeee eeeeeeeeee eeee eeeeeee ee eeeeeeeeeee 8,8-eeeeeeee (M-eeeeeeeeeeeee) eee eeeeeeee. Meeee eeeeeeeeeeeee eeeeeee [8,8]-eeeeeeeeeee eeeeeeeeeeeeee ee eeee eee eeeeeeeee.[‌88‌–‌88‌]

‌Meeeee 8‌ Meeeeeeeeee ee Meeeee-8-eeee eee Meeeeeeee ee Meeeeeeeee[‌8‌–‌88‌]

‌Meeeeeeeeee 8‌

M8	M8	Meeeeeeee Meeee	Meeeee (%)	Mee
Me	Me	eeeeeeeeeeeeeee eeee	88	[‌8‌,‌8‌]
Me	Me	MeMMM	88	[‌8‌]
Me	Me	MMeM8	e.e.	[‌88‌]
Me	Me	eeeeeeeeeeeeeee eeee	88	[‌8‌]
Me	(MM8)88Me	MeM	e.e.	[‌88‌]
Me	MM8Me	MMeM8	e.e.	[‌88‌]
Me	Me	MMMMe	88	[‌88‌]
Me	Me	MMM8MM	88	[‌88‌]
Me	Me	Me8MeMeMeMeMe8	88	[‌88‌]
Me	Me	MMeM8	88	[‌88‌]
Me	Me	MeM	88	[‌88‌]
Me	Me	Me8M	e.e.	[‌88‌]
Me	Me	MeMeM8M	88	[‌88‌]
Me	Me	M8	e.e.	[‌88‌]
Me	8,8-(M8M)8M8M8	MeMe8, MMe	e.e.	[‌88‌,‌88‌]
Me	eMe	Me8	e.e.	[‌88‌]
Me		MMeM8	88	[‌88‌]
Me	(M)-MM=MMMM8Me	MMeM8	8	[‌88‌]
Me	(M)-MM=MMMM8Me	MMeM8	88	[‌88‌]
Me	MM8Me	Me8	e.e.	[‌88‌]
Me	MM8Me	eeeeeeeeeeeeeee eeee	88	[‌88‌]
Me	(MM8)8MM	Me8, MMM8M	88	[‌88‌]
Me	8-MMM8M8	MeM8	88	[‌88‌]
Me	8-MeM8M8	MeM8	88	[‌88‌]
Me	Me	M8	88	[‌88‌]
Me	Me	Me(MMe)8	e.e.	[‌88‌]
Me	eeeeeeeeeeeeeeeee	MeM	88	[‌88‌]
		MM8Me	88	[‌88‌]
MM(MM8MMe)(MM8)8		MeM	88	[‌88‌,‌88‌]
MMe8MM8MMM8MMe8		MeM	e.e.	[‌88‌,‌88‌]
(MM8)8		MeM	e.e.	[‌88‌,‌88‌]
MM(MM8MMMM)(MM8)8		MeM	88	[‌88‌,‌88‌]
MM(MM8MM)(MM8)8		MeM	88	[‌88‌,‌88‌]
MMe8(MM8)8MMe8		MeM	e.e.	[‌88‌,‌88‌]
(MM8)8M(MM8)8		MM8Me	88	[‌88‌]
MMMe(MM8)8MMMe		MeM	e.e.	[‌88‌]
		e-MeMMe	88–88	[‌88‌]

e e.e. = eee eeeeeeee.

Meee eeeeeeeeeeeeeeeeee-8-eeee eeee eeee eeeeeeee ee eeeee ee eeeeeeeeeee eee eeeeeeeeeeeee ee eeeeeeeee eeeeeeeeee eeeeeeeeeeee eeee eee eeee ee eeee eeeeeeee eeeee (‌Meeeee 8‌).[‌88‌,‌88‌] Mee eeeeeeeee ee eeeee eeeeeeeee eeeeeeeee eeee eee eeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeeeee ee eeee eeee eeeeee eeeeee eee eee eeeeeeeeeeee ee eeeeeeeeee ‌8‌ (M8 = M) eeee eeeeeeeeeee eeeeeeeeeeee eeeeee. Meeeeeeeeeee ee eeeeee eeeeeeeeeeee ee eee eee ee eeeeeeeeeee eeeeeeeeee eeeeee eeee ee eeeeeeeeeeeeee[‌88‌] ee eeeeeee.[‌88‌] Mee eeeeeeeee ee eeeeeeeeee ‌8‌ (M8 = Me; M8 = M, Me) eeeeee ee eeeeeeeee ee eeee eeeeee eeeeeee eeeeeeeee eeeeeeeeee eeeeee eeeeee eee eeee eeeeeeee.

‌Meeeee 8‌ Meeeeeeeeee ee Meeeee-8-eeee eeee Meeeeeeeeeee Meeeeeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 8‌

e Meeeeeee eeeeeee eee ee MMM.

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeee-8,8-eee(8-eeeeeeeeeeee)eeeeee-8-eee (‌8‌, M8 = Me; M8 = M); Meeeeee Meeeeeeee:[‌88‌]

Meeeee M: 8-(M-Meeeeeeeeeeeeee)eeeeeee ‌8‌ (M8 = Me; M8 = M; 8.88 e, 88.8 eeee) eee eeeeeeeee ee eee MeMM (888 eM) eeeee eeeee eee eeeeee ee −88°M. M eeee ee eeeee-8,8-eeeeeee (8.88 e, 88.8 eeee) ee eee MeMM (888 eM) eee eeeee eeeeeeee (eeee eeee eee eeeeeeeeeee eee eee eeee eeeee −88°M), eee eeeeeeee eee eeeeeeeee eee 8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eeeee 88°M (eeee eeeeeeeeeee). Mee eeeee eeeeeee eee eeeeeee eeee MMMe8 (888 eM) eee eeeeee eeee 8% MeMM eeee (8 × 888 eM). Mee eeeeeee eeeee eee eeeee (M8MM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee eeeeeee, MM8Me8/MeMM 88:8). Meeeeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8; 8 ×) eeeeeeee eeee eeeeeeee eeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.

References