Ring Opening and C(ω)‐S Coupling: Nickel‐Mediated Transformation of Alicyclic Alkoxyhydroperoxides

Ring Opening and C(ω)‐S Coupling: Nickel‐Mediated Transformation of Alicyclic Alkoxyhydroperoxides Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2025, Volume: 28, Number: 7, Article number : e202401198, Pages count : DOI: 10.1002/ejoc.202401198

Authors

Fomenkov Dmitri I. ¹ , Budekhin Roman A. ¹ , Mulina Olga M. ¹ , Komarova Olga ¹ , Doronin Mikhail M. ¹ , Belyakova Yulia Yu. ¹ , He Liang-Nian ² , Yaremenko Ivan A. ¹ , Terent'ev Alexander O. ¹

Affiliations

1	FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Laboratory for Studies of Homolytic Reactions, Moscow, RUSSIAN FEDERATION
2	Nankai University, State key laboratory of Elemento-Organic Chemistry, Weijin Rd.94, 300071, RUSSIAN FEDERATION

Ozonolysis of cycloalkanone semicarbazones in alcohol containing solution with the subsequent addition of nickel (II) dithiocarbamates or xanthates was found to result in ω-xanthyl or ω-dithiocarbamyl carboxylic acid esters. The reaction proceeds in several steps. The initial one is cycloalkanone semicarbazone ozonolysis in the presence of alcohol, which leads to alicyclic alkoxyhydroperoxide. The second step is an extraordinary interaction between the alkoxyhydroperoxide and nickel (II) dithiocarbamate or xanthate, which proceeds via alkoxy radical formation and its subsequent β-scission, resulting in C−S coupling products. The developed method allows to obtain ω-xanthyl or ω-dithiocarbamyl esters in yields up to 52 % relative to the initial cycloalkanone semicarbazone.

Fomenkov D.I. , Budekhin R.A. , Mulina O.M. , Komarova O. , Doronin M.M. , Belyakova Y.Y. , He L-N. , Yaremenko I.A. , Terent'ev A.O.
Ring Opening and C(ω)‐S Coupling: Nickel‐Mediated Transformation of Alicyclic Alkoxyhydroperoxides
European Journal of Organic Chemistry. 2025. V.28. N7. e202401198 . DOI: 10.1002/ejoc.202401198 WOS OpenAlex

Web of science:	WOS:001407683500001
OpenAlex:	W4406492868

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