Science of Synthesis

Härtinger, S.; Härtinger, M., Science of Synthesis, (2007) 35, 573.

Iodinative decarboxylation of aliphatic carboxylic acids can be achieved by the thermal decomposition of the lead(IV) salts ‌16‌ (‌Scheme 6‌).[‌2‌,‌22‌,‌35‌,‌36‌,‌53‌,‌68‌–‌77‌] The lead(IV) salts ‌16‌ are readily prepared by warming an oxygen-free mixture of lead(IV) acetate with the corresponding acid in an inert solvent. In contrast to the classic Hunsdiecker methods, no particular precaution is necessary to remove traces of water from the reagents and diluents. Without isolation or further purification, lead(IV) salt ‌16‌ is treated with iodine under reflux to liberate carbon dioxide and the iodoalkane ‌17‌. The use of excess iodine and optional irradiation with a tungsten lamp suppresses the oxidative formation of carboxylate side products.[‌69‌,‌74‌] Potassium iodide is an alternative source of iodine;[‌3‌,‌68‌] however, this variation gives lower product yields and generally suffers from the production of large amounts of iodine due to concomitant iodide displacement during iodo complex formation with ‌16‌.

‌Meeeee 8‌ Meeeeeeeeeeeeeeeeee ee Meee(MM) Meeee[‌8‌,‌88‌,‌88‌,‌88‌,‌88‌–‌88‌]

‌Meeeeeeeeee 8‌

M8	Meeeeeeeeee	Meeeee (%) ee ‌88‌	Mee
(MM8)8Me	M8, MMe8, eν, 88°M	888	[‌88‌]
(MM8)88Me	M8, Me8MMMMMe8, eeee, 888°M, 8 e	88	[‌88‌]
eMe	MM, eeeeeee, eeee, 88°M	e.e.	[‌8‌,‌88‌]
	M8, MMe8, eν, 88°M	88	[‌88‌]
	M8, MMM, eν	e.e.	[‌88‌]
	M8, eeeeeee, eν, eeeeee, 8.8 e	88	[‌88‌,‌88‌]
	M8, eeeeeee, eν, eeeeee, 8 e	88	[‌88‌,‌88‌]

e Meeeeeee eeeeeeeeee eee eee eeeeeeeeeeeee ee eee eeee(MM) eeee ‌88‌; eeee = eeeeeeee eeeeeeeee eeeee eeeeeeeee ee eeeeeee eeeee.

e e.e. = eee eeeeeeee.

Meeeeeeeeeee eeeeeeeee

Meeeee 8-Meeeeeeeee-8-eeeeeeeeeee [‌88‌, M8 = 8-(Meeeeeeeeeeeeee)-8-eeeee]; Meeeeee Meeeeeeee:[‌88‌,‌88‌]

MMMMMMM: Meee(MM) eeeeeee ee e eeeeeeeeee eeeeee eeee eee ee eeeee ee eeeeeeeee. Mee eee eeee eeeeeee eee eeee ee eeeeee eeeeeeeeeee ee eeeee.

Me e eee, eeeeeeeeeeee eeee ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee 8-(eeeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee eeee (88 ee, 8.88 eeee) eeee eeeee Me(MMe)8 (888 ee, 8.88 eeee) eee M8 (888 ee, 8.8 eeee). Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88 eee eee eeee eeeeeeee eeeee eeeee eeeeeeeeeee (888-M eeeeeeee eeee). Meeee 8 e, eee eeee eee eeeeee, eeeeeeee, eeeeee eeee ee MeMMM8 (8 × 88 eM), eee eeeee (MeMM8). Meeeeeeeeeeee ee eee eeee eee eeeeeeeeeeee ee eee eeeeeeeeeeeeeeeeeee eeeeeee ee eeeeeeeeeee eeee eee eeeeeeeeeee eeeeee; eeeee: 88 ee (88%); ee 888–888°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 8888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.