2-Alkylidene-2H-indole intermediates. Thermolysis of 2-hydroxydiphenylmethylindole

Dolby, Lloyd J.; Lord, Pierre D.

doi:10.1021/jo01262a042

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Intramolecular Addition Of Benzylic Radicals Onto Ketenimines1

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2022

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Cited by 10 publications

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“…The structural characterization of indoles 8, 9 and 10 relies on their analytical and spectroscopic data. 21 In this respect, the IR spectrum of indole 8 shows a strong absorption at 1706 cm Ϫ1 corresponding to the C᎐ ᎐ O vibration. In the 1 H NMR spectrum of this compound the indolic NH appears as a broad singlet at Scheme 3 Reagents and conditions: (a) t-butyl peroxide (1.2 eq.…”

Section: Intramolecular Addition Of Benzylic Radicals Onto Keteniminesmentioning

confidence: 94%

Intramolecular addition of benzylic radicals onto ketenimines. Synthesis of 2-alkylindoles

2003

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The inter- and intramolecular addition of free radicals onto ketenimines is studied. All the attempts to add intermolecularly several silicon, oxygen or carbon centered radicals to N-(4-methylphenyl)-C,C-diphenyl ketenimine were unsuccessful. In contrast, the intramolecular addition of benzylic radicals, generated from xanthates, onto the central carbon of a ketenimine function with its N atom linked to the ortho position of the aromatic ring occurred under a variety of reaction conditions. These intramolecular cyclizations provide a novel radical-mediated synthesis of 2-alkylindoles.

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Section: Intramolecular Addition Of Benzylic Radicals Onto Keteniminesmentioning

confidence: 94%