Investigation of selective mono-deallylation of O,O'-diallylcatechols and 3-methylene-1,5-benzodioxepanes.
Selective mono-deallylation of O,O'-diallylcatechols using 10% Pd/C was investigated to give the correspond-ing allylphenols. A similar reaction of 3-methylene-1,5-benzodioxepanes afforded O-methacryl catecohols. When substrates bearing various substituents on the benzene ring were subjected to the reaction, regioselective cleavage of an ether bond occurred at the side of para position to an electron-withdrawing group on the aromatic ring. On the other hand, an electron-donating group did not cause any selectivity.
Hayashida
Maiko
M
Faculty of Pharmaceutical Sciences, Tokyo University of Science, RIKADAI, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Ishizaki
Miyuki
M
Hara
Hiroshi
H
D000478:Alkylation; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000498:Allyl Compounds; D002396:Catechols; D010082:Oxepins; D010165:Palladium; D002244:Carbon