AI Article Synopsis
- - The reaction of imidazolylidene-derived enetetramine with aliphatic and certain aryl iodides/bromides leads to the formation of aliphatic aldehydes through a unique one-carbon unit release from the enetetramine.
- - An intermediate compound, 2-alkylimidazoline, is formed during this process, where the alkyl group comes from the substrate and converts into aldehydes after further reactions in acidic conditions.
- - Researchers designed and tested modified substrates to better understand the chemistry of these alkylimidazoline adducts, which yielded significant insights into their behavior and reactions.
Article Abstract
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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3662391 | PMC |
| http://dx.doi.org/10.1021/ja8092746 | DOI Listing |
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Article Synopsis
- - The reaction of imidazolylidene-derived enetetramine with aliphatic and certain aryl iodides/bromides leads to the formation of aliphatic aldehydes through a unique one-carbon unit release from the enetetramine.
- - An intermediate compound, 2-alkylimidazoline, is formed during this process, where the alkyl group comes from the substrate and converts into aldehydes after further reactions in acidic conditions.
- - Researchers designed and tested modified substrates to better understand the chemistry of these alkylimidazoline adducts, which yielded significant insights into their behavior and reactions.
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