Science of Synthesis

Phillips, A. J.; Love, C. E., Science of Synthesis, (2007) 20, 257.

Although several general methods are avaliable for the direct conversion of an acid into the one-carbon higher homologated analogue,[‌67‌–‌70‌] the Arndt–Eistert reaction is the most commonly employed process.[‌71‌,‌72‌]

Mee eeeeeee eeeeeeeee eeeeeeee eeeeeeee ee eeeeeeeeee ee eee eeee ‌88‌ eeee ee eeeeeeeee eeee eeeeeeeeee (eeeeeeeee e eeeee eeeeeeeee ee eeee eeeeeeee) eee eeeeeeeee eeee eeeeeeeeeeee ee eeee ee eeeeeeeeeeee α-eeeee eeeeee ‌88‌. M eeeeeee ee eeeeeeeeeee eeeeeee eeee eeee eeeeeeee ee eeeeeee eee eeeeeeeeeeee eeeee eeeeee eeeeeeeee ­eeeeeeeeeeeeeee eeeeeeee/eeeeeeeeeeee,[‌88‌] 8-eeeeeeeeeeeeeee eeeeeeee/eeeeeeeeeeee,[‌88‌] eee eeeeeeeeeeeeeeeeeeeeeeeeee eeee eeeee eeeeeeeeee eeeeeee eeee eeeee eeeeeeeeeeeee ee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee.[‌88‌] Mee α-eeeee eeeeee ee eeee eeeeeee eeee ee eeeeeee eeeeeeee ee e eeeeee(M) eeee ee eeeeee Meeee eeeeeeeeeeeee eee eeeeeeeeee ee eee eeeeee. Mee eeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeeeee ee eee eeeeeeeee eeeeee[‌88‌] eee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeeeee ee eeeee eeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeee ‌88‌ eee eeeee ee ‌Meeeee 88‌.

‌Meeeee 88‌ Mee Meeee–Meeeeee Meeeeeeeeeee ee Meeeeeeeee Meeee Meeeeeeee eee Meeee Meeeeeeeeeeee ee Meeee Meeeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 88‌

M8	Meeeeeee Meeeeeeeee	Meeeee (%)	Mee
	Me8M, MMM/M8M	88	[‌88‌]
	MeMMe, eeeeeee/M8M	88	[‌88‌]
	MeMM8, MMM/M8M	88	[‌88‌]
	MeMM8, MMM/M8M	88	[‌88‌]
	MeMM8, MMM/M8M	88	[‌88‌]
	MeMMe, M8M/MMM, eeeeeeeeee	88e	[‌88‌]

e Meee ‌88‌ eeeeee eeeeeeeee eeeeee.

e Meee ‌88‌.

Mee eeeeeeee ee eeeeeeeeeeee eeeeeeee eee eeeeeeeee ee eeeee eee eee ee eeee eeeeeee eeeeeeee. Mee eeeeeee, ee e eeee ee eeeeeeeee ee eee eeeeeeeeeeee, eeeeeeeeeeee ee eeee ‌88‌ eeee eeee ‌88‌ eee eeee eeeeeeee ee ee eeee eeeeeeeee ee eee eeee eeeeeeeeeeeeeeee eee eeeeeeeeee eeeeeeee eeee eeeeeeeeeeee eee eeee eeeeee(M) eeeee (‌Meeeee 88‌).[‌88‌] Meee eeeeeeeeeeeeee eeeeeeeeeee eee eeeeeee ee eeeee eeeeeeee/eeeeeeeeee eeeeeeeeee ee eeeeeeeee eeee eeeeeeeeeee, ee eee eeeee eeeeeee eeeeee ee eeee eeeeeee.

‌Meeeee 88‌ Meeee–Meeeeee Meeeeeeeeeee eeee Meeeeeeeeeeeeee Meeeeeee Meeeeeeeee[‌88‌]

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

‌Meeeee 88‌ Meeeeeeeeee ee eeee-Meeeeeeeeeeeee-Meeeeeeee β-Meeeeeee ee Meeee–Meeeeee Meeeeeeeeeee[‌88‌]

Me eeeeeeee ee eeeeeeeeee ee eeeeeee eeeee, eee eeeeeeeeeeeee eeeeeee eeee eeeee eeeeeee ee eeeee eeeee eeee eeee eeeeeee ee eeeee eeeeeeeeeee. Mee eeeeeee, eeeeeeeeeeeeeeeee- eee eeee-eeeeeeeeeeeeee-eeeeeeeee eeeeeee, eeeeee, eee eeeeee eeeeeee eee eeeeeeeeee ee eeeeeeeee eeeeeee ee eeeeee(M) eeeeeeeeeeeeeee/eeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee eeee ee 8-eeeeeeeeeeee-8,8-eeee, 8-eeeeeeeeeeee, eeeeeeeeeeeee, eee eeeeeeeeeee ee eeeeeee eee eeeeeeee eeeeeeee.[‌88‌] Meeeeeee ee eeee eeeeeee eeee ee eeeeeeeeeeeeee eee ee eeeee ee Meeeeee ‌88.8.8.8.88‌

Meeee eeeeeee eeeeeeeee eee eee eeeeee ee eeeeeeee eeeeeeeeeeee ee eeeeeeeeee eeeee eeeeeee e eeeeeee eeeeeeeeeeee,[‌88‌,‌88‌] ee eeeeeeeeeeeeeee eeeeeeeeeeee (eee Meeeeee ‌88.8.8.8.88‌),[‌88‌,‌88‌] eee e 8-[(eeeeeeeeeeeeee)eeeeee]-8M-eeeeeeeeeeeee-eeeee eeeeee.[‌88‌,‌88‌] Meeee eeeeeeeeee eeeee eee eee ee eeeeeeeeeeee, eee eeee eeeeeeeee ee ee eeeeeeeee ee eeeeeee eee ee eeee eeee eeeeee eeeeeeeeee eeeeeeee ee eeeeeeeeee ee eee Meeee–Meeeeee eeeeeeeeeeee.

Meeeeeeeeeee Meeeeeeee

β-Meeee Meeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee, eee ee eeeeee eeeee ee eeeeeeeeee.

Me e eeeeeee eeee ee eee Mee-eeeeeeeee eeeee eeee ‌88‌ (88 eeee) ee eeeee MMM (88 eM) eeee eeeee MeMMMMe (88 eeee) eee Me8M (88 eeee) eeeee ee eeeee eeeeeeeeee ee −88°M. Meeee 88 eee, e eeee ee MM8M8 ee Me8M eee eeeee ee −8°M eeeee eee eeee eeeeee eeeee eeeeeeeee. Meeee 8 e, eee eeeeee MM8M8 eee eeeeeeeee eeee eeeeeee MeMM (8.8 eM), eee eee eeeeeee eee eeeeeee eeee Me8M (88 eM) eee eeeeee eeee eee. MeMMM8, eee. MM8Me, eee eeeee. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeeeee), eeeeee eee eeeee eeeeee eeeeeeeeeeee ee ee eee; eeeee: 88–88%.

Me e eeeeeee eeee ee eee eeeee eeeeee (8 eeee) ee MMM/M8M (8:8; 88 eM) eee eeeee e eeee ee MM8MM8Me (8.88 eeee) ee Me8M (88 eeee) ee −88°M eeeee ee eeeee eeeeeeeeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e, eee eeee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeee eee. MeMMM8 eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 ×). 8 M MMe eee eeeee ee eee eeeeeee eeeee ee 8°M eeeee eee eM eee ee. 8–8 eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 ×). Mee eeeeeee eeeeee eeee eeeeeeeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee (eeeeee eee) eeee eee eeee eeeeeee: eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

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