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2,6‐Epoxy‐3‐benzoxocin‐4‐ol‐Derivate durch zweifache intramolekulare Halbacetalbildung
Author(s) -
Wünsch Bernhard,
Bauschke Gerd
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910110
Subject(s) - chemistry , intramolecular force , substituent , ring (chemistry) , stereochemistry , epoxy , intramolecular reaction , tricyclic , hydrogen bond , epoxide , medicinal chemistry , organic chemistry , catalysis , molecule
2,6‐Epoxy‐3‐benzoxocin‐4‐ol Derivatives by Double Intramolecular Formation of Hemiacetals With dilute HCl the hydroxydialdehyde derivatives 10a‐c are cyclised to give the tricyclic hemiaccetals 6a–c . This double intramolecular formation of hemiacetals succeeds well, if R in 10 is not hydrogen; if R = H an equilibrium betwen 5a and 6a is observed. The 1 H‐NMR data of 6 and 17 support the chair conformation of the 1,3‐dioxane ring bearing an equatorial substituent (OH, OAc) in position 4.