Synthesis and Reactions of 10-Chloro-10,9-(epoxyalkano)selenoxanthenes and 1-Chloro-1-phenyl-3H-2,1-benzoxaselenoles

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10-Chloro-10,9-(epoxyalkano)selenoxanthenes (12,14-17) were prepared by the reaction of 9-(hydroxyalkyl)-selenoxanthenes (4,9-11) with N-chlorosuccinimide, and 1-chloro-1-phenyl-3H-2,1-benzoxaselenoles (32-34) were similarly synthesized. The selenurane structure of 14 was established by X-ray analysis. The proton nuclear magnetic resonance and electron impact mass spectral data supported the selenurane structures of these compounds. Reactions of the selenurane 16 with sodium acetylacetonide gave a selenoxantheniomethanide derivative 37. Thermal reaction of 14 provided 9-(1-chloro-2-hydroxyethylidene)selenoxanthene (41) together with 9-(2-hydroxyethyl)selenoxanthene (9), while thermal reaction in ethanol produced 9-(1-chloro-2-hydroxyethyl)-9-ethoxyselenoxanthene (42). On the other hand, the benzoxaselenole selenurane (32) was heated at 195-200℃ to afford 2-(phenylseleno)benzyl chloride (45), 2-(phenylseleno)benzyl 2-(phenylseleno)benzoate (46) and 2-(phenylseleno)benzaldehyde (28).
社団法人日本薬学会の論文
1990-04-25