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Photochemical Generation of Iminoquinone Methides by 1,4-Hydrogen Migration in Derivatives of o-Tolylnitrene

✍ Scribed by Götz Bucher

Book ID: 102676516
Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 526 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200107)2001:13<2447::aid-ejoc2447>3.0.co;2-n

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✦ Synopsis

The photochemistry of a series of derivatives of o-tolyl azide, bearing a variety of substituents in the benzylic positions, has been investigated using matrix isolation spectroscopy and density functional calculations. It has been found that introduction of any substituent possessing a lone pair (i.e., R = Br, Cl, MeO, Me 2 N) allows a 1,4-hydrogen shift to take place, yielding iminoquinone methides. Additional methyl groups in the benzylic position, however, do not promote a photochemical conversion into iminoquinone methides. If the benzylic substituent itself is part of a ring system, the size of [a

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