Photolabile protection of alcohols, phenols, and carboxylic acids with 3-hydroxy-2-naphthalenemethanol.
Irradiation of alcohols, phenols, and carboxylic acids "caged" with the (3-hydroxy-2-naphthalenyl)methyl group results in fast (k(release) approximately = 10(5) s(-1)) release of the substrates with good quantum (Phi = 0.17-0.26) and chemical (>90%) yields. The initial byproduct of the photoreaction, 2-naphthoquinone-3-methide, reacts rapidly with water (k(H2O) = 144 +/- 11 s(-1)) to produce parent 3-hydroxy-2-naphthalenemethanol. The o-quinone methide intermediate can be also trapped by other nucleophiles or converted into a photostable Diels-Alder adduct with ethyl vinyl ether.
Kulikov
Anton
A
Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
Arumugam
Selvanathan
S
Popik
Vladimir V
VV
D000438:Alcohols / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D045563:Indolequinones; D009281:Naphthalenes / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D010777:Photochemistry / Q000379:methods*; D014867:Water / Q000737:chemistry
D000438:Alcohols; D002264:Carboxylic Acids; D045563:Indolequinones; D009281:Naphthalenes; D010636:Phenols; D014867:Water; C068040:quinone methide; C055629:2-naphthalenemethanol