Regioselectivity of aryl radical attack onto isocyanates and isothiocyanates
文献信息
发布日期
2018-11-14
DOI
10.1039/C8OB02209G
影响因子
3.876
作者
Geethika K. Weragoda, Rowan L. Pilkington, Richard A. J. O'Hair
查看原文
摘要
The combination of multistage mass spectrometry experiments employing the distonic radical approach together with DFT calculations are used to examine addition of the N-methyl-pyridinium-4-yl radical cation (γ-NMP) to iso(thio)cyanates in the gas-phase. The type of products formed depend on the nature of the iso(thio)cyanate: (1) hydrogen atom abstraction occurs for alkyl isocyanates; (2) aryl isocyanates undergo radical-ipso substitution; (3) radical attack occurs at the CC bond of allyl isocyanate; (4) radical attack occurs at the CS bond of isothiocyanates to generate S adducts of γ-NMP and isonitriles. DFT calculations provide insight into the reactivity differences of these heterocumulenes towards the electrophilic C-centered γ-distonic radical cations. Translation of these gas phase results to the solution phase were hampered by dominating radical recombination reactions which appear to be favoured over the radical-iso(thio)cyanate reactions.
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来源期刊
Organic & Biomolecular Chemistry
CiteScore:
3.4
自引率:
10.3%
年发文量:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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