Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

• Oleg A. Levitskiy,
• Olga I. Aglamazova,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

• recently, two publications from the Werz group appeared concerning anodic activation of donor–acceptor cyclopropanes followed by their functionalization with arenes [43] or yielding oxy-ketones or 1,2-dioxanes [44]; the latter process was inspired by a previous report of Buriez [45]. The anodic

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• -diketones 283 (Scheme 84) [359][360]. The Kornblum–DeLaMare rearrangement of 1,2-dioxenes 284 [361], 1,2-dioxanes 286 [362], and tert-butyl peroxides 288 [330][363] produces 1,4-dicarbonyl compounds 285, 287, and 289, respectively (Scheme 85). These compounds are versatile starting substrates for the

Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst

• Nathan J. Gesmundo and
• David A. Nicewicz

Beilstein J. Org. Chem. 2014, 10, 1272–1281, doi:10.3762/bjoc.10.128

• irradiation in the presence of oxygen, bicyclic endoperoxides were obtained [12]. Formation of the 1,2-dioxanes was presumed to occur via single electron oxidation of the diene by the excited state DCA followed by either 6-endo or 7-endo cyclization modes to generate a fleeting distonic cation radical species

• was observed 2w. Conclusion In the presence of an organic single electron photooxidant, a variety of dienes were demonstrated to undergo a cyclization/endoperoxidation cascade sequence to form 1,2-dioxanes. Requirements for successful diene reactivity are the presence of an oxidizable olefin and an

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

• .10.6 Abstract The present review describes the current status of synthetic five and six-membered cyclic peroxides such as 1,2-dioxolanes, 1,2,4-trioxolanes (ozonides), 1,2-dioxanes, 1,2-dioxenes, 1,2,4-trioxanes, and 1,2,4,5-tetraoxanes. The literature from 2000 onwards is surveyed to provide an update

• , and antitumor agents. Keywords: cyclic peroxides; 1,2-dioxanes; 1,2-dioxenes; 1,2-dioxolanes; ozonides; 1,2,4,5-tetraoxanes; 1,2,4-trioxanes; 1,2,4-trioxolanes; Introduction Approaches to the synthesis of five and six-membered cyclic peroxides, such as 1,2-dioxolanes I, 1,2,4-trioxolanes (ozonides

• ) II, 1,2-dioxanes III, 1,2-dioxenes IV, 1,2,4-trioxanes V, and 1,2,4,5-tetraoxanes VI, published from 2000 to present are reviewed. These compounds are widely used in synthetic and medicinal chemistry (Figure 1). In the last decade, two reviews on this rapidly progressing field were published by