Jc. Schmidhauser et al., PRODUCTS FROM THE ACID-CATALYZED REACTION OF CYCLIC MONOTERPENES AND PHENOL, Journal of organic chemistry, 60(12), 1995, pp. 3612-3618
Nine phenol-containing products from the acid-catalyzed reaction of ph
enol and gamma-terpinene were isolated and identified. A combination o
f X-ray crystallographic and spectroscopic techniques was used to assi
gn the structures of the three p,p-bisphenols, two og-bisphenols, two
bicyclic monophenols, and two bicyclic phenyl ethers. Several of the i
ndividual reaction products interconverted under acid-catalyzed condit
ions. The same nine products were formed using 3-carene, alpha-pinene,
Limonene, or sabinene in place of gamma-terpinene, although the relat
ive concentrations of these products varied depending upon the startin
g monoterpene's structure. A mechanism is proposed which accounts for
the products' structures and reactivities.