17675-89-7Relevant academic research and scientific papers
A Scalable Process for the Synthesis of 1,2-Dialkyldiselanes and 1-Alkaneselenols
Cooksey, John P.,Kocieński, Philip J.,Blacker, A. John
supporting information, p. 2571 - 2575 (2019/11/14)
A four-step telescoped process for the synthesis of 1-alkaneselenols entails (1) the rapid formation of potassium selenocyanate from potassium cyanide and selenium in methanol, (2) the nucleophilic substitution of bromoalkanes or alkyl tosylates with potassium selenocyanate, (3) the mild base-catalyzed conversion of the resultant 1-alkaneselenocyanates to 1,2-dialkyldiselanes (the Krief reaction), and (4) the reduction of the resultant 1,2-dialkyldiselanes with hypophosphorous acid to give the desired 1-alkaneselenols. The process has been used to produce 1-octaneselenol on a 10.4 mol scale. Nine examples of the process are described.
Synthesis of hexylselenol and hexylselenides from hexylthiol involving hexylthiolanium salts
Krief, Alain,Dumont, Willy,Robert, Michael
, p. 2601 - 2604 (2008/09/16)
Selenium nucleophiles react regioselectively at the endocyclic or exocyclic carbon of hexylthiolanium salts depending upon the nature of the salt. Georg Thieme Verlag Stuttgart.
Synthesis of primary-alkyl selenols and selenides from primary-alkyl thiols involving diphenyl sulfonium salts
Krief, Alain,Dumont, Willy,Robert, Michael
, p. 2167 - 2168 (2007/10/03)
Hexyl thiol has been transformed to hexyl selenol and related selenides and selenocyanate by substitution of the corresponding hexyldiphenylsulfonium tetrafluoroborate with selenium nucleophiles. The Royal Society of Chemistry 2005.
Conditions-driven selective synthesis of selenides and selenols from elemental selenium
Krief, Alain,Trabelsi, Mahmoud,Dumont, Willy,Derock, Michel
, p. 1751 - 1754 (2007/10/03)
Sodium borohydride in DMF is able to reduce elemental selenium in the presence of ethanol. Alkylation of the species resulting from the reaction of 2:1 molar equivalents of NaBH4/Se allows the selective synthesis, under very mild conditions, of symmetrical dialkyl selenides. Addition of formic acid, prior to that of the electrophile, permits the synthesis of the corresponding selenols.
