Selenocyanation of Aryl and Styryl Methyl Ketones in the Presence of Selenium Dioxide and Malononitrile: An Approach for the Synthesis of α-Carbonyl Selenocyanates

Abstract

Single-crystal XRD data of 3a and copies of 1 H and 13 C NMR of all synthesized compounds (PDF)Accession Codes CCDC 2041476 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

Organic Selenocyanates: Rapid Advancements and Applicationsin the Field of Organic Chemistry

“…[43] In 2020, Marpna and coworkers also established a similar approach for the selenocyanation of aromatic ketones (118/ 119) using the combination of SeO 2 with CH 2 (CN) 2 as the SeCN initiator. [44] The technique was performed with aryl methyl ketones (118 a-118 i) efficiently under optimized condition, endured by miscellaneous considerable substituents (e. g., 4-Me, 2-OMe, 4-F, 3-Cl, 2-Br, 3-NO 2 , 2,4-dimethoxy, 2,4,6-trimethyl), and usually delivered the intended α-carbonyl selenocyanates (120 a-120 i) in moderate to good yields (Scheme 61a). The procedure was moreover acceptable to further heteroaryl methyl ketones compounds such as 1-(furan-2-yl)propan-1-one (118 j) and 1-(thiophen-2-yl)propan-1-one (118 k).…”

“…[44] The reaction began with the enolization of ketone (118), which was accompanied by a nucleophilic attack of enolate ketone (118 A) on the electrophilic selenium atom of TSD, a selenocyanating reagent prepared by the reaction of SeO 2 with CH 2 (CN) 2 , resulting in the creation of αcarbonyl selenocyanates 120 (Scheme 62). [44]…”

“…Using the selenocyanating reagent, various styryl methyl ketones ( 119 a – 119 e ), including substituents with para and ortho positions, produced good yields of the corresponding selenocyanates products ( 121 a – 121 e ). Note that isobutenyl methyl ketone ( 119 f ) was also compatible to give the expected product ( 121 f ) in a 46% yield, but no selenocyanated product was formed when heteroaryl styryl methyl ketone was used as a substrate (Scheme 61b) [44] . The reaction began with the enolization of ketone ( 118 ), which was accompanied by a nucleophilic attack of enolate ketone ( 118 A ) on the electrophilic selenium atom of TSD, a selenocyanating reagent prepared by the reaction of SeO 2 with CH 2 (CN) 2 , resulting in the creation of α‐carbonyl selenocyanates 120 (Scheme 62).…”

Ag/SeO2/C Avalanche Type Resonant Tunneling Schottky Barriers

“…They also find applications as electrocatalysts 2 . Literature data reported thousands of articles about many technological applications that benefits from selenium dioxide as selenating agent under simple reacting conditions 3 . However, articles which consider SeO 2 as a solid compound suitable for electronic applications are almost absent.…”

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO2: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

“…It was observed that the course of the SeO 2 -mediated reaction is dictated by the nature of the acid as well as the solvent used in a particular set of reactions. Thus, as part of our ongoing research on the synthetic utility of selenium dioxide in organic synthesis, ,, we wish to report here a direct and efficient one-step protocol for the synthesis of oxygen-based fused heterocyclic compounds (3a-aryldihydro-[1,3]­dioxolo­[4,5- d ]­[1,3]­dioxole-2,5-diyl)­bis­(phenylmethanones) by self-condensation of arylglyoxals derived from arylketones in the presence of SeO 2 and trifluoroacetic acid (TFA) (Scheme b).…”