By Professor Dr. Alain Krief, Professor Dr. László Hevesi (auth.)
During the final fifteen years organoselenium chemistry underwent a incredible mutation: from an unique region of technological know-how practised by means of a couple of experts it grew to become a comparatively good mastered and usual method of man-made natural chemistry. the major to this good fortune is reasonable variety of selenium dependent reagents and reactions were came across, that are in a position to practice particular adjustments selectively and infrequently less than very gentle stipulations. the purpose of this quantity is to provide the several selenium containing reagents now to be had to chemists, to say the scope in addition to the restrictions in their reactions, and to match 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
Seq. PhSeHl20°c/lh nPrCH=OICH0 3 PhSeHl20°c/lh • 92% (PhCHz}zNH 87% (PhCHz}3N 93% PhCHzNHCHzPr 86% I)PhCH=OISeq. 2h CHzPh ------------------------. 2eq. Pent-CH=OIPhSeHlCHOylO°c/6h 'Hex PhCH=O/PhSeH I Me 81% 91% Scheme 48 [ISO] tertiary amines bearing three different substituents on nitrogen [150, 151] (Scheme 48e). 7 Reduction of Aldehydes and Ketones to Alcohols Hydrogen selenide [153, 178] and bromomagnesium benzeneselenolate  reduce the carbonyl group of aldehydes and ketones and produce the corresponding alcohols.
This reaction involves ammonium hydrogen selenide as the effective catalyst . Its course is altered when performed under forced conditions [NEt3, 100 DC, 50 kg/cm2] since formanilides are produced instead of the ureas  (Scheme 70c). 025 eq. 4 Synthesis of Tetraalkyl Ureas The process of the formation of ureas from dialkyl amines is drastically changed from that described with primary ones. The amine salts of selenocarbamates are still produced in the first stage of the reaction. They are stable under nitrogen at 25 DC but are susceptible to molecular oxygen already at 0 DC and lead to bis (N ,N-dialkylcarbamoyl)diselenides in almost quantitative yields  (Scheme 71).
These reactions have been used for the synthesis of terminal and a, f3disubstituted olefins from a series of dihalogenoalkanes [138-140] (Schemes R2 X Rl'~. X / c-c R a) Br R 2, N~Se ~"R X b) / 3 R ,- c=c 1 4 Solventlf("C) , R4 . 2 Hydrogen Selenide, Selenols, Selenocyanates, ... and Related Compounds X Rl Rl~" R1, ,R4 C=C, R I' R3 . 1 2eq. 'R R3 4 CI 22- THF-HMPT (3/1) 80°C R2)==