Science of Synthesis

Kostikov, R. R.; Khlebnikov, A. F.; Sokolov, V. V., Science of Synthesis, (2010) 47, 821.

The pyrolysis of amine oxides constitutes a reliable synthesis of unrearranged alkenes. Its importance in this regard, however, has largely been reduced by the development of the Wittig alkenation reaction. Nevertheless, this so-called Cope elimination still plays a role in the degradation of naturally occurring nitrogen-containing compounds (see also Houben–Weyl, Vol. 5/1b, pp 238–249).[‌181‌]

Meee eeeeeeeeeee ee eeeeeeeeeeeee eeee eee M-eeeee ee eeeeeeee eeeeee eeeeee eeee eeeeeee ee 888–888°M, eeeeeeeee ee ee eeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌,‌888‌] Me ee ee eeeeeeeeeee ee eee Meeeeee eeeeeeeeeee eee eeeeeeee eee e eeee-eeeeeeee eeeeee eeeeeeeeee eeeeeeeee ‌88‌ ee e eee eeeeeeeeeee. Meeee M-eeeeee eee eeeeee ee eeeeeeee eeee eeeeee ee eeeeeeeee eeee eeeeeeee eeeeeeee ee 8-eeeeeeeeeeeeeeeeeee eeee, ee ee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeeee (‌88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeee M-Meeeee eee Meeeeeeee Meeeee Meeeeeeee[‌888‌,‌888‌]

Meee eeeeee ee eeee eee eee eeeeeeeee ee eee-8-eeee, eeeeeeeeeeeeeeee, eeeeeeeeeeeeeeeeeeeee, eee eeeeeee eeeeeeeeeeee. Mee eeeeeeeee ee eeeee M-eeeeee eeee e eeeeeeee eeeeeeeeee eeeeeee eeeee eeeeeeee ee eeeeeee eeeeeeeeee eeee- eee eeeeeeeee eeeeee eeeee, eeeeeeeee ee eee eeee ee eee eeee (‌Meeee 88‌).[‌888‌,‌888‌–‌888‌] Mee eeee ee eeeeeeeeeee ee eeeeeeeeeeeeee eeee eeeeeeeeee M-eeeeee eeeeeee eeee eee eeeeee ee eee eeeee eeeee: eeee-eeeee >> eeeeeeee ≈ eeeeeeeee ≈ eeeee > eeeee > eeeeeeeee > eeeee > eeeeee.[‌888‌]

‌Meeee 88‌ Meeeeeeee ee Meeeeee eeee Meeee M-Meeeee ee eee Meee Meeeeeeeeee[‌888‌,‌888‌–‌888‌]

Meeeeeee Meeeeeee	e	Meeeeee(e)	Meeee (%)	Mee
	–		88	[‌888‌]
	–		88e	[‌888‌]
	–		88	[‌888‌]
	–		88	[‌888‌]
	–		88	[‌888‌]
	–		88	[‌888‌]
	–		88	[‌888‌]
	–		88 + 88	[‌888‌]
	8		88	[‌888‌]
	8		88	[‌888‌]
	8		88	[‌888‌]
	8		88	[‌888‌]
	8		88	[‌888‌]
	8		88	[‌888‌]
	8		88–88	[‌888‌]
	8		88	[‌888‌]
	8		88	[‌888‌]
	8		88	[‌888‌]
	8		88 + 8	[‌888‌]
	8		8 + 88	[‌888‌]
	8		88 + 88	[‌888‌]
	8		88–88 + 8–8	[‌888‌,‌888‌]
	8		88 + 8 + 8	[‌888‌]
	8		88 + 88 + 8	[‌888‌]

e Meeee eeeee ee eeeeeeee eeeee.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeeeeeee-M,M-eeeeeeeeeeeeeeeeeee (88.8 e, 8.88 eee), 88% M8M8 (88.8 e, 8.88 eee), eee MeMM (88 eM) eee eeeeee ee e 8.8-M Meeeeeeeee eeeee, eeeeeee eeee e eeeee eeeee, eee eeeeeee ee eeeee ee ee. Meeee 8 e, eee eeeee eeeee ee eeeeeeeeee 8 e, 88% M8M8 (88.8 e eeee eeee) eee eeeee, eeee eeeeeeee. Mee eeee eee eeeeeee ee eeeee ee ee eee ee eeeeeeeeee 88 e, eeeeeeeee eeeeee eeeeeeee eee eeeeeeeee ee eee eeeeeeee eeeeeeee (eeeeeeee) ee e eeeee eeeeee ee Me eeeee. Meeeeeeee ee M8 eeeeeeeee eeeeeeeee eeeeeeee eeeeeeeeeeeee ee eee eeeeee eeeeeeee.

Mee eeeeeee eee eeeeeeee eeee e 8.8-M eeeee-eeeeeeee eeeee, eee MeMM eee M8M eeee eeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee (eeee eeeeeeeeeee 88–88°M) eeeee eee eeeeeeee eeeee eeeee eeeeeee eeeeeeeeee. Mee eeeee eee eeeeee eeee e eeeeeeee eeeeeee eee e eeeee Meeeeee eeeeee, eee eee eeeeeeeee eeeee eee eeeeee ee e eee eee/eeeeeee eeee. Mee eeeee eee eeeeee (eee eeee) ee 88–888°M, eee eeeeeee eeeeeeee (~88 Meee) eee eeeeeee, eeee eeeeeeee. Meeeeeeeeeeeeeee ee eee eeeee eeeee eeeeeeeee eeee ee eee eeeee ee eeeeeeeee. Meeeeeeee, eee eeee eeeeeeeeeee eee eeeeee ee 888°M, eee eeeeeeeeeeeee ee eee eeeee eeeee eeeeeeee eeee eeeee 8 e. Mee eeeeeeeeee eee eeeee eeee M8M (888 eM), eee eee eeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeee eeee M8M (8 ×), eee-eeee 88% MMe (8 ×), eee MeMMM8 eeee, eeeeee eeee 8-eM eeeeeeee. Mee eeeeeee (eee eee/eeeeeee) eeeeee eee eeeeeeee eeeeeee Meeee eeee eee eeeeeeeee eeee e eeeee eeeee ee Me; eee eeeeeee eee eeeeeeeee ee 888–888°M; eeeee: ee. 88 e (ee. 88%).

References

Meeeeee Meeeeeeeeee

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