Decomposition of a 1-hydroperoxynaphthalen-2(1H)-one by bases
Abstract
The decomposition of 1-hydroperoxy-1-isopropylnaphthalen-2(1H)-one (1) by various bases has been studied. Complex redox and rearrangement processes lead to 1-hydroxy-1-isopropylnaphthalen-2(1H)-one (11), the trans-epoxide (12) of this enone, and the rearrangement product (14) of that epoxide, along with r-3,4-epoxy-3,4-dihydro-c-2-hydroxy-2-isopropylnaphthalen-1(2H)-one (15) and an acid resulting from oxidation and ring cleavage. Both intra- and inter-molecular oxygen transfers between the hydroperoxy and enone groups probably occur.