207619-53-2Relevant academic research and scientific papers
Reactions of Anodically Generated Methoxystilbene Cation Radicals: The Influence of Ortho-Substituted Vinyl and Formyl Groups
Chong, Kam-Weng,Thomas, Noel F.,Low, Yun-Yee,Kam, Toh-Seok
, p. 7279 - 7290 (2019)
The present investigation represents a continuation of studies on the effect of ortho′-substitution on the reactivity of anodically generated methoxystilbene cation radicals. Whereas previous studies have focused on the effect of ortho′-substituted nucleophilic groups such as OH, NH2, CH2OH, CH2NH2, and COOH, the present study extends the investigation to ortho′-substituted vinyl and formyl groups. The results show that when the ortho′-substituent is a vinyl group, the products include a bisdihydronaphthalene derivative and a doubly bridged, dibenzofused cyclononane from direct trapping of a bis carbocation intermediate. In the presence of an additional 3-methoxy substituent, the products are the tetracyclic chrysene derivatives. When the ortho′-substituent is a nonnucleophilic formyl group, the products include fused indanylnaphthalenes and indanylbenzopyran aldehydes. When an additional 3-methoxy group is present, an unusual fused benzofluorene-dibenzoannulene product is obtained. Mechanistic rationalization for the formation of the various products is presented. The results have contributed to a deeper understanding of how the reactivity of the methoxystilbene cation radicals is affected by the nature of the ortho′-substituents.
Synthesis of o-Dialkenylbenzenes and Indenes Using Heck and Oxypalladation Reactions
Braese, Stefan,Ruemper, Joerg,Voigt, Katharia,Albecq, Stephane,Thurau, Gert,et al.
, p. 671 - 678 (2007/10/03)
o-Bromostyrenes 2-Br react with various alkenes in the presence of palladium catalysts to give either substituted indene 6 or o-diethenylbenzene derivatives 3, depending on the reaction conditions.Under oxidative conditions the latter can be cyclized to indene derivatives as well. - Keywords: Cross-coupling, Heck; Palladium catalysis; Indanes; Arenes, dialkenyl-N
