Abstract
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.
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For preceding communication, see [1]. The series “N-Hetarylethylenes” comprises 9-alkenyl-carbazoles, 10-alkenylphenothiazines, and 10-alkenylphenoxazines.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12,. pp. 1674–1678, December, 1988.
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Anfinogenov, V.A., Khlebnikov, A.I., Filimonov, V.D. et al. N-hetarylethylenes. 1. Synthesis and isomerization of 10-allyland 10-propenylphenoxazines. Chem Heterocycl Compd 24, 1384–1387 (1988). https://doi.org/10.1007/BF00486685
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DOI: https://doi.org/10.1007/BF00486685