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

• –d is proposed to occur through intermediate peroxy ester 150 (Scheme 43). 1,2-Dioxolanes and related cyclic systems have attracted considerable attention from synthetic chemists as they may be used for the preparation of biologically active compounds. Under acidic conditions, 3-hydroxy-1,2

• -dioxolanes 151 are rearranged similarly to the Criegee mechanism into diketone derivatives 152 (Scheme 44) [298]. Unlike the Baeyer–Villiger rearrangement, in which only mono-O-insertion can take place, the Criegee rearrangement of peroxide 153 in an acidic medium and under solvent-free conditions does not

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

• ][227][228]. The present review covers literature relating to 5- and 6-membered cyclic peroxide chemistry published between 2000 and 2013. Review 1. Synthesis of 1,2-dioxolanes The modern approaches to the synthesis of 1,2-dioxolanes are based on the use of oxygen and ozone for the formation of the

Re₂O₇-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles

• Wantanee Sittiwong,
• Michael W. Richardson,
• Charles E. Schiaffo,
• Thomas J. Fisher and
• Patrick H. Dussault

Beilstein J. Org. Chem. 2013, 9, 1526–1532, doi:10.3762/bjoc.9.174

• ], we needed to prepare a number of 3-alkoxy-1,2-dioxolanes. Brønsted acid-promoted etherification of hemiacetals (1,2-dioxolan-3-ols) required harsh conditions and proceeded in good yields only for unhindered alcohols [18]. We were curious whether Re2O7, a catalyst known to activate alcohols via a