Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 18, Pages 6475-6479Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8092746
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Funding
- EPSRC
- Engineering and Physical Sciences Research Council [EP/E012191/1, EP/E036244/1] Funding Source: researchfish
- EPSRC [EP/E012191/1, EP/E036244/1] Funding Source: UKRI
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Reaction of imidazolylidene-derived enetetramine 2 with aliphatic iodides and bromides (and with aryl iodides bearing alkene-containing side-chains in the ortho-position) leads to formation of aliphatic aldehydes through an unprecedented extrusion of a one-carbon unit from the enetetramine. An intermediate 2-alkylimidazoline 24 is proposed, where the alkyl group derives from the substrate; this imidazoline undergoes further reaction in situ to afford the observed aldehydes on acidic workup. Modified substrates were designed and prepared to probe the chemistry of the alkylimidazoline adducts and provided extensive information on the chemistry of the adducts.
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