Radical addition reactions. Part II. The addition of ethyl cyanoacetate to conjugated olefins

Huang, R.L. and Ong, Chong Oon and Ong, S.H. (1968) Radical addition reactions. Part II. The addition of ethyl cyanoacetate to conjugated olefins. Journal of the Chemical Society C: Organic. pp. 2217-2221. ISSN 0022-4952, DOI https://doi.org/10.1039/j39680002217.

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Official URL: https://doi.org/10.1039/j39680002217


The addition of ethyl cyanoacetate, catalysed by t-butyl peroxide at 155-160°, to a series of conjugated olefins XCH:CHY, namely dimethyl fumarate (X = Y = CO2Me), methyl crotonate (X = Me, Y = CO 2Me), β-methyl-styrene, methyl cinnamate, benzylideneacetone, and cis- and trans-cinnamonitrile (X = Ph, Y = Me, CO2Me, Ac, or CN, respectively), gives mainly the 1:1-adduct, XCHR·CH2Y (R = CH(CN)·CO2Et), in the first two cases, and XCH 2·CHRY in the others, in yields of 26, 53, 42, 31, 16, 26, and 20%, respectively. Isomerisation of cis-cinnamonitrile to the trans-isomer under the conditions of the reaction is interpreted as due to the reversibility of the addition step. This, however, does not occur in the addition of butanal to the same nitrile, which gives PhCH2·CH(CN)·COPr n (40%).

Item Type: Article
Additional Information: Huang, R.L., Ong, C.-O., Ong, S.H. Department of Chemistry, University of Malaya, Malaysia.
Uncontrolled Keywords: Radical addition reactions; ethyl cyanoacetate; conjugated olefins
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 02 Nov 2020 01:59
Last Modified: 02 Nov 2020 01:59
URI: http://eprints.um.edu.my/id/eprint/25597

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