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- W1557777842 abstract "The phenylseleno group (PhSe) has evolved in recent years as a very useful and versatile functionality. Its facile introduction into organic molecules and its subsequent oxidative or reductive removal, has allowed many important synthetic transformations.1–7 Due to the fact that, similarly to halogens, it can exist either as an electrophilic species (PhSe+) or as a nucleophilic one (PhSe-), this group can be introduced either via nucleophilic substrates (e.g. carbanions, olefins), or via electrophilic ones (e.g. epoxides, halides), as illustrated in Scheme 1. Another valuable aspect of the phenylseleno group is that it can be readily oxidized to the corresponding selenoxide(PhSe(O)—), which undergoes β-hydrogen abstraction and syn-elimination to form olefins, under relatively mild conditions (Scheme 2(a)). Furthermore, this group can be substituted with hydrogen, upon the action of an appropriate reducing agent (Scheme 2(b)). The great synthetic utility of the phenylseleno group is apparent from its extensive utilization in numerous natural products syntheses,1 as well as many other synthetic studies.2–7" @default.
- W1557777842 created "2016-06-24" @default.
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- W1557777842 date "1985-01-01" @default.
- W1557777842 modified "2023-10-18" @default.
- W1557777842 title "N-phenylselenophthalimide (NPSP)" @default.
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- W1557777842 doi "https://doi.org/10.1016/s0040-4020(01)96722-5" @default.
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