The synthesis of 5-hydroxy chromenes

The synthesis of 2,2-dimethyl-5-hydroxychromene ( 1 d) is described. The synthesis of the analogous 5,7-dihydroxy derivatives, using similar conditions, yields the adduct 9 derived via a Bucherer type reaction. X-ray analysis of 9 demonstrated that a pyrrolidine group was in the 7-position, and that...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 63; no. 10; pp. 2589 - 2596
Main Authors ApSimon, J. W, Herman, L. W, Huber, C
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.10.1985
National Research Council of Canada
Subjects
Chemistry
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Organic compounds
Physics
Preparations and properties
Structure of solids and liquids; crystallography
Structure of specific crystalline solids
Wittig reaction
Molecular structure
Review
Experimental study
Oxygen heterocycle
X ray diffraction
Bicyclic compound
Phenols
Aromatic compound
Intramolecular hydrogen bond
Organic compounds
Hydrogen bond
Crystalline structure
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Summary:The synthesis of 2,2-dimethyl-5-hydroxychromene ( 1 d) is described. The synthesis of the analogous 5,7-dihydroxy derivatives, using similar conditions, yields the adduct 9 derived via a Bucherer type reaction. X-ray analysis of 9 demonstrated that a pyrrolidine group was in the 7-position, and that the 5-hydroxyl group was involved in a strong intramolecular hydrogen bond to the 4-keto oxygen atom.
ISSN:0008-4042
1480-3291
DOI:10.1139/v85-430