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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 7, Number 6
BKCSDE 7(6)
June 20, 1986

Title	Reactions, Hydrogenation and Isomerization of Unsaturated Esters with a Rhodium(Ⅰ)-Perchlorato Complex
Author	Hyun Mok Jeong, Chong Shik Chin*
Keywords
Abstract	The isolated products from the reactions of Rh(ClO4)(CO)(PPh3)2 (1) with CH2 = CHCO2C2H5 (2) and trans-CH3CH = CHCO2C2H5 (3) contain 80∼ 90% of [Rh(CH2 = CHCO2C2H5)(CO)(PPh3)2]ClO4 (4) and [Rh(trans-CH3CH = CHCO2C2H5(CO)(PPh3)2]ClO4 (5), respectively where 2 and 3 seem to be coordinated through the carbonyl oxygen. It has been found that complex 1 catalyzes the isomerization of CH2 = CH(CH2)8CO2C2H5 (6) to CH3(CH2)nCH = CH(CH2)7-nCO2C2H5 (n = 0∼7) under nitrogen at 25℃. The isomerization of 6 is slower than that of CH2 = CH(CH2)9CH3 to CH3(CH2)nCH = CH(CH2)8-nCH3 (n = 0∼8), which is understood in terms of the interactions between the carbonyl oxygen of 6 and the catalyst. It has been also observed that complex 1 catalyzes the hydrogenation of 2, 3, 6, trans-C6H5CH = CHCO2C2H5 (7), CH3(CH2)7CH = CH(CH2)7CO2C2H5 (8) and CH2 = CH(CH2)9CH3 (9), and the isomerization (double bond migration) of 6 and 9 under hydrogen at 25℃. The interactions between the carbonyl oxygen of the unsaturated esters and the catalyst affect the hydrogenation in such a way that the hydrogenation of the unsaturated esters becomes slower than that of simple olefins.
Page	468 - 471
Full Text	PDF

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