16509-44-7Relevant articles and documents
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Kupchan,S.M.,Afonso,A.
, p. 2217 - 2218 (1960)
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Hydrogenolysis of Small Cycloalkanes, XI. - Hydrogenation of Bicyclobutane-1- and -2-carboxylates
Hertzsch, Winfried,Musso, Hans
, p. 1485 - 1491 (2007/10/02)
Hydrogenation of ethyl bicyclobutane-2-carboxylate (1) with Pd/C in ethanol at normal conditions leads to 95 percent of ethyl 2-methylbutyrate (2) and 5 percent of ethyl n-valerate (3).The corresponding 1-carboxylic acid ester 8 yields 99 percent of 2 but less than 1 percent of cyclobutane as well as the cis- and trans-2-methylcyclopropanecarboxylates 5 and 9.In this case 2-methylenebutyric and cis- and trans-2-methylcrotonic acid esters (10, 11a, and 12) can be detected as intermediates.From these, conclusions can be made about the mechanism at the catalyst. 5 is the main product with a poisoned catalyst.
Lewis Acid Enhancement of Photochemical Trans -> Cis Isomerization of α,β-Unsaturated Esters
Lewis, Frederick D.,Oxman, Joe D.
, p. 7345 - 7347 (2007/10/02)
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