Science of Synthesis

Schobert, R.; Hölzel, C.; Barnickel, B., Science of Synthesis, (2010) 47, 46.

The Horner (also known as Wittig–Horner) reaction, named after Leopold Horner, employs phosphine oxide anions instead of phosphorus ylides to alkenate aldehydes and ketones.[‌353‌] For that purpose an alkyl-substituted diphenylphosphine oxide ‌96‌ is first treated with potassium tert-butoxide or sodium amide and then with the carbonyl compound to give the alkene ‌97‌. When a lithium base is used, the corresponding β-hydroxyphosphine oxide ‌98‌ may be isolated (‌Scheme 34‌). Since the one-step version of the Wittig–Horner reaction mainly leads to E-alkenes ‌97‌, it is covered in Section ‌47.1.1.1.4.2‌.

‌Meeeee 88‌ Mee Meeeee Meeeeeee[‌888‌]

Meeee Meeee eee ee-eeeeeee eeee eee eeeee ee eeeeee eeeeeeeee eeeeeeeeeee eeeee eeee eee Meeeee eeeeeeee eeeee eeeeeeeeee eeee eeeeeeeee eeeeeee ee eeeeeeeee eeeeee,[‌888‌,‌888‌] eeee Meeeee eee ee-eeeeeee eeeeeeeee eee Meeeee eeeeeeee eeee e eeeeee eee eeeeeeeee eeeeeeeeee eeeeee. Meee eeeeee eeeeeeee ee eeeeeeeee eee eeeeeeeeee ee eee eeeee eeeeeeeeeee eeeeeeeeeeeeee β-eeeeeeeeeeeeeeee eeeeee.[‌888‌] Meeeeeeeeeee eeeeeeeeeeeeeeeeeee eee eeee eeeeeeee eeee eeeeeeee eeeeeeee eeee ee 8,8-eeeeeeeeeeeeeee ee eeeeeeeeeeeeeee eee eeee ee eee eeeeeeeeeeee. Mee eeeeeee/eeeee eeeeeeeeeee eeee eeeeeee ee eee eeeee eeeeeeeeeeee eeeeeeee ee eee eeeeeeeee eeeee. Meeeeeee eeeeeeeeeeeee eeee ee eeeeeeeee ee eeeeeeeeee eeeeeeee eee eeeeeee eeeeeeeeeee eee eeeeee eeeeee ee eeeeeeeeee ee eeee ee eee eeeeeeee ee eeeeeee ee eee eeeeee eeeeee.[‌888‌,‌888‌] Meeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee ee eee β-eeeeeeeeeeeeeeee eeeee eeeeeee eeeeeee eeeee eeeeee ee eeee eeeeeee, eee eeee eeeeeee-‌888‌ eee eeeee-‌888‌. Meeee eeee eeeeeee eeeeeee eee eeeeeeeeeee eeeee eeeeeeee ee eee eeeeee eeee (eeeeeeeee eeeeee eeeeeee), eee eeeeeee-eeeeee eeeeee eee M-eeeeee (M)-‌888‌ eee eee eeeee-eeeeee eeeeee eee M-eeeeee (M)-‌888‌ eeeeeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ M-Meeeeeeee Meeeee–Meeeee Meeeeeeeee[‌888‌,‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

M8	M8	Meeee (eeeeeee/eeeee)	Meeee (%) ee eeeeeee-‌888‌	Meeee (M/M)	Meeee (%) ee (M)-‌888‌	Mee
Me	(MM8)8Me	88:88	88	–e	88	[‌888‌]
Me	Me	88:88	88	88:8	88	[‌888‌]
Me	Me	88:88	88	88:8	88	[‌888‌]
(MM8)8Me	Me	88:88	88	88:8	88	[‌888‌]
	Me	88:88	88	–e	88	[‌888‌]
(MM8)8MM	Me	88:88	88	–e	88	[‌888‌]
		eeeeeee eeee	88	–e	88	[‌888‌]

e Meeeeee eeeee eeee M-eeeeee.

Meeeeeee e eeeeeeee eeee,[‌8‌,‌888‌] eeeeeeeeee ee eeeeeee eeeeeee eeeeeeeee,[‌888‌–‌888‌] eee Meeeee–Meeeee eeeeeeee eeeeeeee eee eeeee eeee eeee eee Meeeee eeeeeeee eeeeeeeee eee eeeeeeeeee ee eee β-eeeeeeeeeeeeeeee eeeee eeeeeee. Mee eeeeeeeeee eee eee eeeee eeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeeeeeeeee eeee eeeee ee eeee eeeeee eeeeeee ee eeeeeeeeee ee eee eeeeeee eeeee eeee eeeee, eee eee eeeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeeee eeeee eeeeee. Meee eee eeee eeeeee eeeeeeeeeeee ee eeeeeeeeee Meeeee eeeeeeeee ee eeeeeeee eeeeeeeee eeee eee eee eeeee eeee Meeeee-eeee eeeeeeeeeeee, e.e. ee Meeeeeee’e eeeeeeeee ee eeeeeeeeee M.[‌888‌,‌888‌] Mee Meeeee–Meeeee eeeeeeee eeeeee eeeee eeee eee eee eeee eeeeeeeee eee M-eeeeeeeee eeeeeeeeeee (eee Meeeeee ‌88.8.8.8.8.8‌).

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-[(8M)-eeee-8-eeee]-8,8-eeeeeeeee [(M)-‌888‌, M8 = 8-(8-Meeeee-8,8-eeeeeeee-8-ee)eeeee; M8 = Me]; Meeeeee Meeeeeeee:[‌888‌]

Meeee e M8 eeeeeeeeee, 8.88 M MeMe (8.8 eM, 88.8 eeee) eee eeeee ee e eeee ee eeeeeeeee eeeee ‌88‌ [M8 = 8-(8-eeeeee-8,8-eeeeeeee-8-ee)eeeee; 8.8 e, 88.8 eeee] ee eeeee MMM (88 eM) ee 8°M. Meeee 88 eee, eee eeeeee eeee eee eeeeee ee −88°M eee eeeeeee eeee e eeee ee eeeeeeeeeeee (8.8 e, 88.8 eeee) ee MMM (88 eM) eeeeeeeee eeee MeMe. Mee eeeeeeeeeee eeee eee eeeeeee ee eeee ee ee, eee eee. ee MM8Me (88 eM) eee eeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM, 8 × 88 eM), eee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eee eee eeeeeeee eeee eeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe) eeee eeeeeee-‌888‌ ee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M (MeMMe); Me 8.88 (MeMMe).

88% MeM ee eee (888 ee, 8.88 eeee) eee eeeee ee e eeee ee eeeeeee eeeeeee-‌888‌ [M8 = 8-(8-eeeeee-8,8-eeeeeeee-8-ee)eeeee; 8.88 e, 8.88 eeee] ee MMM (88 eM). Mee eeeeeee eee eeeeee ee 88°M eee 8 e eee eeee eeeeee eeee e eeeeeee ee Me8M (88 eM) eee M8M (88 eM). Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM), eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 888 ee (88%); ee 88–88°M (88 Meee).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 888.