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1-Dodecene, 1-iodo-, (1E)-

Base Information Edit
  • Chemical Name:1-Dodecene, 1-iodo-, (1E)-
  • CAS No.:66553-46-6
  • Molecular Formula:C12H23I
  • Molecular Weight:294.219
  • Hs Code.:
  • Mol file:66553-46-6.mol
1-Dodecene, 1-iodo-, (1E)-

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Homogeneous catalytic aminocarbonylation of 1-iodo-1-dodecene. The facile synthesis of odd-number carboxamides via palladium-catalysed aminocarbonylation

10.1016/j.tet.2008.08.022

This research investigates the synthesis of odd-number carboxamides through palladium-catalysed aminocarbonylation of (E)- and (Z)-1-iodo-1-dodecene. The study aims to extend the scope of aminocarbonylation to open-chain iodoalkenes, which are easily accessible from even-number aldehydes, to produce odd-number linear carboxamides that are less common in nature. Key chemicals used include various amine nucleophiles such as tert-butylamine, piperidine, morpholine, and glycine methyl ester, along with the iodoalkene substrate synthesised from 1-dodecanal via a hydrazone intermediate. The reactions were performed under atmospheric and high-pressure carbon monoxide conditions using palladium(II) acetate and triphenylphosphine as catalysts. The study concludes that the chemoselectivity of the reaction towards forming conjugated unsaturated carboxamides or alkyne-type amides depends on factors like the type of amine used and carbon monoxide pressure. The findings provide an efficient method for functionalising open-chain iodoalkenes and offer a straightforward route to synthesise higher carboxamides from readily available aldehydes, contributing to the field of synthetic chemistry and potentially aiding in the development of new pharmaceuticals and materials.

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