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Intramolecular Diels‐Alder Reaction of Furans with Allenyl Ethers Followed by Phenylthio and Trialkylsilyl Groups Rearrangement
Author(s) -
Chuang ChiTe,
Yen ChiaHui,
Wu HsienJen
Publication year - 1998
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199800119
Subject(s) - chemistry , intramolecular force , ether , propargyl , furan , diels–alder reaction , diene , intramolecular reaction , medicinal chemistry , organic chemistry , catalysis , natural rubber
A new reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by phenylthio group rearrangement was discovered. Treatment of the propargyl ethers 2a‐c with t ‐BuOK in t ‐BuOH at 85 ° C gave the phenylthio group rearrangement products 5a‐c and 6a‐c . A reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by trialkylsilyl group rearrangement is also demonstrated.