Interrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds

Interrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2024, Volume: 89, Number: 8, Pages: 5699-5714 Pages count : 16 DOI: 10.1021/acs.joc.4c00233

Authors

Yaremenko Ivan A. ¹ , Fomenkov Dmitri I. ¹ , Budekhin Roman A. ¹ , Radulov Peter S. ¹ , Medvedev Michael G. ¹ , Krivoshchapov Nikolai V. ¹ , He Liang-Nian ² , Alabugin Igor V. ³ , Terent’ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991, Russian Federation
2	State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
3	Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States

Four heteroatoms dance in the cascade of four pericyclic reactions initiated by ozonolysis of C═N bonds. Switching from imines to semicarbazones introduces the fifth heteroatom that slows this dance, delays reaching the thermodynamically favorable escape path, and allows efficient interception of carbonyl oxides (Criegee intermediates, CIs) by an external nucleophile. The new three-component reaction of alcohols, ozone, and oximes/semicarbazones greatly facilitates synthetic access to monoperoxyacetals (alkoxyhydroperoxides).

Yaremenko I.A. , Fomenkov D.I. , Budekhin R.A. , Radulov P.S. , Medvedev M.G. , Krivoshchapov N.V. , He L-N. , Alabugin I.V. , Terent’ev A.O.
Interrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds
Journal of Organic Chemistry. 2024. V.89. N8. P.5699-5714. DOI: 10.1021/acs.joc.4c00233 Scopus OpenAlex

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OpenAlex:	W4393407726

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