Journal
TETRAHEDRON LETTERS
Volume 53, Issue 31, Pages 3974-3976Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.05.082
Keywords
Photoreaction; alpha-Hydroxy-o-quinodimethanes; Hetero-Diels-Alder reaction; o-Tolualdehydes; Trifluoromethyl ketones
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Hetero-Diels-Alder reaction of alpha-hydroxy-o-quinodimethanes photochemically generated from o-tolualdehydes with trifluoromethyl ketones gave a mixture of hemiacetals and hydroxyaldehydes in fairly good yields. Their subsequent oxidation with PCC provided 1-isochromanones as formal oxidative [4+2] cycloaddition products. In contrast, similar reaction of aromatic ketones such as o-methylbenzophenone, 1-indanone, and alpha-tetralone gave exclusively the corresponding ketones having (trifluoromethyl)methylol groups at the o-position. (C) 2012 Elsevier Ltd. All rights reserved.
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