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Synthesis 1992; 1992(8): 761-764
DOI: 10.1055/s-1992-26221
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o-(α-Benzotriazolylalkyl)phenols: Novel Precursors of o-Quinone Methides

Alan >r. Katritzky* , Xiangfu Lan
  • *Department of Chemistry and Center for Heterocyclic Compounds, University of Florida, Gainesville, Florida, 32611-2046, USA
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Publication Date:
17 September 2002 (online)

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1-[α-(Benzotriazol-1-yl)alkyl]-2-napthols and 2-[(benzotriazol-1-yl)-methyl]phenols have been shown to lose a molecule of benzotriazole to generate o-quinone methides, which can be trapped with electron-rich olefins (ethyl vinyl ether, 1-vinyl-2-pyrrolidinone) to afford chroman derivatives, i.e. 2,3-dihydro-1H-naphtho[2,1-b]pyrans and 3,4-dihydro-2H-1-benzopyrans, respectively.