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Notizen/Notes Kronenether aus o ‐Chinondiaziden und Oxetan
Author(s) -
Kirmse Wolfgang,
Lelgemann Rudolf
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240825
Subject(s) - oxetane , chemistry , oxonium ion , nucleophile , intramolecular force , medicinal chemistry , quinone , polymer chemistry , ion , stereochemistry , organic chemistry , catalysis
Crown Ethers from o ‐Quinone Diazides and Oxetane The carbenes 11 , generated by photolysis of the di‐ and tetrachloro‐ o ‐quinone diazides 10 , react with oxetane in a 1:3 ratio to give the 15‐membered crown ethers 19 . In the presence of methanol, the oxonium ions 12 are trapped with formation of 1‐(aryloxy)‐3‐methoxypropanes ( 13 ). In the absence of additional nucleophiles, 12 reacts with oxetane until the chain length is appropriate for inverting intramolecular attack of the aryl oxide at the α‐carbon atom of the oxonium ion ( 18 → 19 ).