Catalytic oxidative carbonylation of primary and secondary diamines to cyclic ureas. Optimization and substituent studies

…, M Kokka, L McElwee-White

Index: Qian, Fang; McCusker, Jennifer E.; Zhang, Yue; Main, A. Denise; Chlebowski, Mary; Kokka, Michiyo; McElwee-White, Lisa Journal of Organic Chemistry, 2002 , vol. 67, # 12 p. 4086 - 4092

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Citation Number: 54

Abstract

W (CO) 6-catalyzed oxidative carbonylation of 1, 3-propanediamine to the corresponding urea has been examined under a variety of conditions. Following optimization, the Thorpe- Ingold effect on ring closure was studied using 2, 2-dialkyl-1, 3-propanediamines. For the 2, 2-dimethyl-and 2, 2-dibutyl-1, 3-propanediamines, the yields were increased significantly as compared to that of the unsubstituted case. The eight-membered cyclic urea 5-butyl-5- ...