1,3-methoxy rearrangement of masked o-benzoquinones: a novel synthesis of p-quinol ethers.
p-Quinol ethers are valuable synthons in synthetic organic chemistry. MOBs 1a-1i can be converted to p-quinol ethers 2a-2i in a highly efficient manner via 1,3-methoxy migration catalyzed by Lewis acids. The migration was found to be reversible and dependent on the electronic effect of substituent R3 of MOBs.
Yang
Ching-Shun
CS
Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan.
Liao
Chun-Chen
CC
D000143:Acids / Q000737:chemistry; D016227:Benzoquinones / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006873:Hydroquinones / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D012997:Solvents
D000143:Acids; D016227:Benzoquinones; D004987:Ethers; D006873:Hydroquinones; D012997:Solvents; D010100:Oxygen