Science of Synthesis

Kostikov, R. R.; Khlebnikov, A. F.; Sokolov, V. V., Science of Synthesis, (2010) 47, 848.

Although the synthesis of alkenes by deamination of aziridines has been mentioned in Houben–Weyl, Vol. 5/1b, p 753 and in a review,[‌203‌] one cannot consider this method as being convenient and general. In most cases, aziridines are much less readily available than the corresponding simple alkenes. However, since alkylaziridines with free NH groups can be prepared from alkenes with inversion of the original alkene configuration, and the subsequent deamination can be achieved with retention, the overall process provides an alkene with inverted configuration.[‌203‌] For such deamination protocols, nitrosyl chloride and alkyl nitrites (with cheletropic extrusion of nitrous oxide) or the not so easily available difluoroamine (via N-nitrenes with loss of nitrogen) have been proposed. For an analogous “isodiazene” process, the oxidation of N-aminoaziridines ‌142‌ with manganese(IV) oxide, nickel(II) peroxide, or tert-butyl hypochlorite has been described; in some cases, the intermediary 3,4-dihydro-1,2-diazetes ‌144‌ can be isolated along with the alkenes ‌143‌ (‌Scheme 53‌).[‌203‌,‌323‌]

‌Meeeee 88‌ Meeeeeeee ee M-Meeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

M8	M8	Meeeeeeeee	Meeeee (%) ee ‌888‌	Meeeee (%) ee ‌888‌	Mee
Me	Me	e-MeMMe, 8,8-ee-eeee-eeeeeeeeeeeee, MM8Me8, −88°M; ee MeM8, MM8Me8, −88°M	e.e.	8	[‌888‌]
		e-MeMMe, 8,8-ee-eeee-eeeeeeeeeeeee, MM8Me8, −88°M	88	88	[‌888‌]
		e-MeMMe, 8,8-ee-eeee-eeeeeeeeeeeee, MM8Me8, 88°M	e.e.	8	[‌888‌]
		MeM8, MM8Me8, −88°M	88e	88e	[‌888‌]
		MeM8, MM8Me8, 88°M	e.e.	8	[‌888‌]

e e.e. = eee eeeeeeee.

e Me MMM.

Meeeeeeeeeee Meeeeeeee

8,8′-Meeeeeeeeeeeeeee (‌888‌, MM8M8 = 8-Meeeeeeeeeeeee); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: eeee-Meeee eeeeeeeeeeee ee eeeeee eeeee eee eeee- eee eeeee-eeeeeeeee. Mee eeeeeeeeee eeeeee ee eeeeeeeee ee e eeee-eeeeeeeeee eeee; eeee eee eeee eeeeee ee eeee eeeeeeeee.

Me M-eeeeeeeeeeeeee ‌888‌ (MM8M8 = 8-eeeeeeeeeeeeee; 88 ee, 8.88 eeee) ee eeeeeeeeeeee MM8Me8 (8 eM) eeee ee −88°M eee eeeee 8,8-ee-eeee-eeeeeeeeeeeee (88 ee, 8.88 eeee). Mee eeee eee eeeeeee eeee e-MeMMe (88 ee, 8.888 eeee), eeeee eeee e eeeeeee. Meee eee eeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeeeee. Mee eeeeeee eee eeeeeee ee −88°M eee 8.8 e eee eeee eeeeeee ee eeee ee ee. Mee eeeeeee eee eeeeeeeeee, eeeeeee e eeeeeeeee eeeee, eeeee eee eeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee 8:8) ee eeee eee eeeeeee; eeeee: 88.8 ee (88%); ee 888–888°M; eee eee eeeeeeeee ‌888‌ (MM8M8 = 8-eeeeeeeeeeeeee); eeeee: 88.8 ee (88%). Meee eee eeeeeeee eee eeeeeee eee ee ee, eee eeee eeeeeee eeeeeeee eee 8,8′-eeeeeeeeeeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 888.