Metal-free direct oxidation of α-isophorone to ketoisophorone by I2 under photoirradiation
Ji-qing Bao , Li-hua Chen , Rui-ren Tang , Lin-ying Cao , Shan Liang
Journal of Central South University ›› 2012, Vol. 19 ›› Issue (10) : 2755 -2759.
Metal-free direct oxidation of α-isophorone to ketoisophorone by I2 under photoirradiation
Molecular iodine was first utilized for direct oxidation of α-isophorone (α-IP) to ketoisophorone (KIP) with molecule oxygen at room temperature and the effects of amount of iodine, solvents and reaction time were investigated extensively. The optimized result shows that 70.2% conversion of α-isophorone and 82.6% selectivity of ketoisophorone are obtained with 15% iodine (molar fraction) in acetonitrile under photoirradiation for 5 h. Moreover, the possible mechanism is proposed.
ketoisophorone / aerobic oxidation / iodine / reaction mechanism
| [1] |
|
| [2] |
|
| [3] |
KAZUHARU S, NOBORU K, TOMOHIRO K, YASUO M. Method for preparation of trimethylhydroquinone from isophorone: JP, 11255706 [P]. 1999-12-08. |
| [4] |
BONRATH W, SCHNEIDER M. Manufacture of trimethylhydroquinone diacylates: US, 7153994 [P]. 2006-12-26. |
| [5] |
FIBRICE A, BONRATH W. Process for the preparation of 2,3,5-trimethylhydroquinone diesters: US, 0123720 [P]. 2007-05-31. |
| [6] |
KILL S, HUTHMACHER K. Process for the production of 2,3,5-trimethylhydroquinone diesters: US, 6417409 [P]. 2002-07-09. |
| [7] |
|
| [8] |
BECKER J J, HOCHSTRASSER U P, SKORIANETZ W. Process for the preparation of oxophorones: US, 3,944,620 [P]. 1976-03-16. |
| [9] |
WIDMER, MUNCHENSTEIN C H, EAST BRIGHTON A U. Ketoisophorone manufacture: US, 3,960,966 [P]. 1976-06-01. |
| [10] |
|
| [11] |
|
| [12] |
|
| [13] |
|
| [14] |
|
| [15] |
|
| [16] |
|
| [17] |
YADAV J S, REDDY B V S, RAO C, SABITHA V, REDDY M J. Molecular iodine-catalyzed highly stereoselective synthesis of sugar acetylenes [J]. Synthesis, 2003(2): 247–250. |
| [18] |
|
| [19] |
|
| [20] |
|
| [21] |
|
| [22] |
|
| [23] |
|
/
| 〈 |
|
〉 |