An article Understanding the Reactivity of Group 6 Metal (M = Cr, W) Alkynyl Fischer Carbene Complexes with Multi-Reactive Masked Dienes WOS:000459821300017 published article about DIELS-ALDER REACTIONS; CYCLOADDITION REACTION; ORGANIC SYNTHESES; ELECTRON-TRANSFER; (1-ALKYNYL)CARBENE COMPLEXES; REGIOSELECTIVE SYNTHESIS; CYCLIZATION REACTIONS; CATALYZED REACTIONS; ANTHRONE; CHROMIUM(0) in [Collado, Alba; Gomez-Gallego, Mar; Santiago, Alicia; Sierra, Miguel A.] Univ Complutense, Fac Quim, Dept Quim Organ 1, Ctr Invest Quim Avanzada ORFEO CINQA, E-28040 Madrid, Spain in 2019, Cited 75. Application In Synthesis of Anthrone. The Name is Anthrone. Through research, I have a further understanding and discovery of 90-44-8
Group 6 alkynyl Fischer carbene complexes behave as electrophiles with highly reactive masked dienes such as anthrone and 3-hydroxy-2-pyrone, which also can react as bidentate nucleophiles. Both Cr-0 and W-0 alkynyl carbene complexes require tertiary amines to promote the formation of 1,4-C-addition products, but a marked dependence of the reactivity on the metal was observed. Although W-0 complexes form exclusively the 1,4-C-adducts in the presence of a catalytic amount of base, Cr-0 complexes lead to new anthrone-derived bis-carbene complexes, obtained by a sequential 1,4-C- and 1,4-O-addition process with high diastereoselectivity and only in the presence of an excess of base. DFT computational studies show that the gap between the LUMO of the complex and the HOMO of the anthrone determines the differences in reactivity and that the stability of the intermediate metal allenyls formed after the initial 1,4-addition is decisive for the outcome of the reaction.
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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem