Alkylation of phenoxazine with allyl bromide has given 10-allylphenoxazine. The prototropic isomerization of 10-allylphenoxazine in DMSO on treatment with t-BuOK, KOH, and NaOH has been examined. At elevated temperatures, mixtures of cis- and trans-10-propenylphenoxazines are formed, but at room temperature in the presence of t-BuOK isomerization proceeds stereoselectively to give cis-10-propenylphenoxazine. The influence of temperature and reaction times on the isomeric composition of the 10-propenylphenoxazines has been studied. The cis-propenylphenoxazine obtained in the kinetically controlled reaction isomerizes under the reaction conditions to the equilibrium mixture of cis- and transisomers of 10-propenylphenoxazine.
ASJC Scopus subject areas
- Organic Chemistry