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The role of substituents in retro Diels-Alder extrusion of CO2 from 2(H)-pyrone cycloadducts
Abdullahi, Mohamed H. Thompson, L.M. Bearpark, M.J. Vinader, Victoria
Abdullahi, Mohamed H.
Thompson, L.M.
Bearpark, M.J.
Vinader, Victoria
Publication Date
06/10/2016
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26/07/2016
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Abstract
An experimental and computational investigation is conducted into the role of substituents in retro Diels-Alder extrusion of CO2 from 2-oxa-bicyclo[2.2.2]oct-5-en-3-ones. We provide the first experimental evidence that loss of CO2 from the cycloadducts significantly depends on the nature and position of the substituents. For example, we show that whilst 5-carboethoxy-2-pyrone undergoes a more facile cycloaddition that 3-carboethoxy-2-pyrone, the cycloadduct from the latter pyrone undergoes a more facile loss of CO2 than the cycloadduct from the former pyrone.
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Abdullahi MH, Thompson LM, Bearpark MJ et al (2016) The role of substituents in retro Diels–Alder extrusion of CO2 from 2(H)-pyrone cycloadducts. Tetrahedron. 72(40): 6021-6024.
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