Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

• alkylidenecyclopropanes 142 for the synthesis of polycyclic benzazepine derivatives 144 (Scheme 29) [123]. The authors noted electron-withdrawing substituents were detrimental to the efficacy of the reaction with electron-withdrawing N-substituents failing to react. When a methoxy group was installed at the para-position

Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes

• Guillaume Ernouf,
• Jean-Louis Brayer,
• Christophe Meyer and
• Janine Cossy

Beilstein J. Org. Chem. 2019, 15, 333–350, doi:10.3762/bjoc.15.29

• , 145 chemin des lilas, 59310 Beuvry-la-Forêt, France 10.3762/bjoc.15.29 Abstract Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished

• stereoselective access to a wide variety of heterosubstituted and/or functionalized alkylidenecyclopropanes which would not be readily accessible by other strategies. The different [2,3]- and [3,3]-sigmatropic rearrangements of cyclopropenylcarbinol derivatives disclosed to date, as well as the analysis of their

• substrate scope and some applications of the products arising from those reactions, are presented in this review. Keywords: alkylidenecyclopropanes; cyclopropanes; cyclopropenes; sigmatropic rearrangements; strained rings; Introduction Among the ever expanding diversity of chemical transformations

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

• Yu Liu,
• Qiao-Lin Wang,
• Zan Chen,
• Cong-Shan Zhou,
• Bi-Quan Xiong,
• Pan-Liang Zhang,
• Chang-An Yang and
• Quan Zhou

Beilstein J. Org. Chem. 2019, 15, 256–278, doi:10.3762/bjoc.15.23

• oxidation and dehydrogenation gives the target product 49. A new and first achievement for the synthesis of CF3-contained seven-membered ring compounds 55 and 56 through trifluoromethylation of acrylamide-tethered alkylidenecyclopropanes 54 was presented by Shi and co-workers (Scheme 13) [78]. The possible

• alkylidenecyclopropanes 1 with allylic bromides 78 for the synthesis of 2-bromo-1,6-dienes 79 via radical ring-opening and SH2’ reactions (path V in Scheme 17) [95]. The experimental results suggested that radical carbonylation could also be incorporated in the reaction sequence, leading to 2-bromo-1,7-dien-5-ones 80

• -tethered alkylidenecyclopropanes). Rh(II)-catalyzed oxidative radical ring-opening and cyclization of MCPs. Ag(I)-catalyzed oxidative radical amination/ring-opening/cyclization of MCPs derivatives. Heating-promoted radical ring-opening and cyclization of MCP derivatives (arylvinylidenecyclopropanes) with