By Professor Dr. Alain Krief, Professor Dr. László Hevesi (auth.)
During the final fifteen years organoselenium chemistry underwent a dazzling mutation: from an unique region of technological know-how practised by way of a couple of experts it turned a comparatively good mastered and everyday technique of artificial natural chemistry. the main to this good fortune is reasonable variety of selenium dependent reagents and reactions were stumbled on, that are capable of practice particular differences selectively and sometimes lower than very light stipulations. the purpose of this quantity is to provide the several selenium containing reagents now on hand to chemists, to say the scope in addition to the constraints in their reactions, and to check these which own comparable reactivities. The authors current the reagents within the order of accelerating oxidation point round the selenium atom.
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Additional info for Organoselenium Chemistry I: Functional Group Transformations
PhSeSiM~ CH2CI 2 or THF o (PhCH1 CH1h Te = 0 US'Ph 92% 2eq. PhSeSiM~ .. 2 Hydrogen Selenide, Selenols, Selenocyanates, ... and Related Compounds Me3SiSeSiMe3 RzX=O R=Ph X=Se 96% R=Ph X=Te 89% R=Bu X=Se 62% o I" ~ " RzX THF/20°C/ Ih rS'M. 5 Reduction of Nitro-, Nitroso-, Hydroxylamino-, Azo- and Hydrazo-aromatic Compounds to Aromatic Amines and Reduction of Aryldiazonium Salts to Hydrazinium Salts Hydrogen selenide reduces nitrobenzene to aniline quantitatively  (Scheme 42a). Similar results are observed when nitrobenzene, or other title compounds are reacted with carbon monoxide, water and triethylamine in the presence of catalytic amounts of selenium  (Scheme 42) (see also Sect.
S!. 0' ~ en lg ()Q I ~ a. 2 Hydrogen Selenide, Selenols, Selenocyanates, ... MeOH R -Nonyl ~ R Se 58 0 C,18h 100% R = (CH2hC02Me 58°C,18h .. 5h Ph ~ 100%  KSeCNlMeOH 25°C,16h o 0 o 0 X X 64%  KSeCN MeOHireflux 30%  Scheme 30 trifluoroacetic acid is monitored  by IH NMR (Scheme 32). These reactions have been successfully applied to the synthesis of terminal [145, 147, 169] and a, fJ-disubstitutedolefins [144,146,147,169] includingstilbenes [144,146,147,167, 169], cyclohexenes [144, 146, 164, 169] (Schemes 30, 31) and unsatured sugars  (Scheme 30, Entry d) from the corresponding epoxides.
Compounds bearing quaternary centres are also aromatized by selenium at around 340°C by loss of one of the two groups (Schemes 63a, b, d, 64) [197, 199-201,210]. With this respect ethyl groups seem to be more prone to removal than methyl groups (Scheme 64) . Angular alkyl groups present in polycyclic derivatives are also lost and this occurs preferentially with respect to the cleavage of one of the rings (Schemes 63d, 65b, c) [204, 208, 209]. Again an angular ethyl group is more prone to removal than a methyl group.
Organoselenium Chemistry I: Functional Group Transformations by Professor Dr. Alain Krief, Professor Dr. László Hevesi (auth.)