Skip to main content
. Author manuscript; available in PMC: 2010 Jan 16.
Published in final edited form as: J Org Chem. 2009 Jan 16;74(2):730–738. doi: 10.1021/jo8021132

Table 1.

Oxidation of α,β-Unsaturated Carbonyl Compounds by T-HYDRO® catalyzed by Rh2(cap)4.a

Entry Substrate Product Equiv.
TBHP
%Yield b
1 graphic file with name nihms91280t1.jpg graphic file with name nihms91280t2.jpg 10.0
8.0
84
76
2 graphic file with name nihms91280t3.jpg graphic file with name nihms91280t4.jpg 10.0 76
3 graphic file with name nihms91280t5.jpg graphic file with name nihms91280t6.jpg 10.0 87
4 graphic file with name nihms91280t7.jpg graphic file with name nihms91280t8.jpg 10.0
8.0
85
82
5 graphic file with name nihms91280t9.jpg graphic file with name nihms91280t10.jpg 8.0 65
6 graphic file with name nihms91280t11.jpg graphic file with name nihms91280t12.jpg 8.0 70
7 graphic file with name nihms91280t13.jpg graphic file with name nihms91280t14.jpg 8.0 64
8 graphic file with name nihms91280t15.jpg graphic file with name nihms91280t16.jpg 8.0 32
a

Reactions were performed with 1.36 mmol of substrate in 2.5 mL of DCE to which was added 4.0 or 5.0 equiv of TBHP (70% in water) and 0.50 mol % Rh2(cap)4 and the solution was heated at 40 °C. After 16 hours an additional 4.0 or 5.0 equiv of TBHP (70% in water) and 0.50 mol % Rh2(cap)4 was added, and reaction was continued for an additional 24 hours.

b

Isolated yield after column chromatography; carboxylic acids were purified by recrystallization from ethyl acetate and the mass yield after recrystallation is given.