Untersuchungen an Selen‐Verbindungen. XLVI. Aliphatische Selenoxide und Selenone. Aliphatische Selenoxide und Selenone

Abstract

Durch Ozonisierung von Dialkylselenoxiden werden die aliphatischen Selenone SeO2R2 mit R  CH3, C2H5, n‐C3H7, n‐C4H9 erhalten. Die Darstellung der Dialkylselenoxide erfolgt durch Umsetzung von Dialkylselendibromiden mit Silberoxid in Methanol. Es werden einige Eigenschaften der Dialkylselenoxide und ‐selenone mitgeteilt und im Lichte der aus IR‐Spektren abgeleiteten Bindungsverhältnisse diskutiert, wobei insbesondere Eigenschaftsunterschiede herausgestellt werden.

Human indole(ethyl)amine-N-methyltransferase (hINMT) catalyzed methylation of tryptamine, dimethylsulfide and dimethylselenide is enhanced under reducing conditions - A comparison between 254C and 254F, two common hINMT variants

“…Expansion of spectra region where oxidized DMSe products would occur. C. Table: Spectra peaks determined for the present study (FTIR) matched to previously published cm -1 values (referenced) for (upper) DMSe [24, 25] and (lower) oxidized DMSe products dimethyl selenone (DMSeO 2 ) and dimethyl selenoxide (DMSeO) [26]. DMSeO 2 and DMSeO were not found in the spectra (arrows indicate where they would occur).…”

A General and Efficient Method To Convert Selenides into Selenones by Using HOF·CH3CN

“…Dialkyl selenones are somewhat different, as the fully oxidized products, as well as the intermediate selenoxides, are sensitive to thermal eliminations and nucleophilic substitutions. The preparation of dibutyl selenone ( 2b ), for example, has been previously achieved in two steps through the ozonolysis of dibutyl selenoxide ( 3b ), which in its turn was prepared by separate oxidation of 1b 26. The mild conditions by which the HOF · CH 3 CN oxidation proceeds eliminates any side reaction, and when 1b served as the reactant, 2b was formed quantitatively after 5 min.…”

Selenium stabilized carbanions. .alpha.-Lithio selenoxides as reagents for the synthesis of olefins, allyl alcohols, and dienes

“…The reactions of -lithio selenoxides with electrophiles are summarized in Scheme I. The intermediate selenoxides (11)(12)(13) are normally not isolated but are directly converted to olefins by selenoxide syn elimination or to selenides by reduction.…”

“…1 -phenyl-1,3-pentadiene37 was prepared by following the procedure given for (£)-1 -phenyl-1 -pentene (run 2) from 0.263 g (1 mmol) of benzyl phenyl selenoxide and 0.200 g (1.25 mmol) of l-bromo-3methyl-2-butene in 88% yield purified by short-path distillation (bath temperature 60-65 °C, 0.2 mm); NMR 1.83 (broad s, 6 H), 5.9 (d, J = 11 Hz, 1 H), 6.29 (d, J = 15 Hz, 1 H), 6.83 (dd, y = 15, 11 Hz, 1 H), 7.0-8.4 (m, 5 H); IR 3030,2910,1642,1595,1450,692 cm-1.…”