Chemistry Letters, Vol.36, No.4, 516-517, 2007
Effect of intramolecular hydrogen bonding on thermolysis of dioxetane: Unusual instability of bicyclic dioxetanes bearing a hydroxynaphthyl group with vicinal substitution pattern
Dioxetanes bearing a 1-hydroxynaphthalen-2-yl group 4(OH) or 2-hydroxynaphthalen-1-yl group 5(OH) were found to be significantly unstable thermally in contrast to their methoxynaphthyl-analogs 4(OMe) and 5(OMe). The marked instability of 4(OH) and 5(OH) was attributed to the intramolecular hydrogen bonding of a hydroxy group on the naphthalene ring.