Epoxidation of 4,5-dialkyl-2,3-dihydro-1Н-phosphole 1-oxides
- 42 Downloads
A method was developed for the synthesis of 1,5-dialkyl(cycloalkyl,phenyl)-2-phenyl-6-oxa-2-phosphabicyclo[3.1.0]hexane 2-oxides from alkynes, involving the epoxidation of unsaturated cyclic organophosphorus compounds with m-chloroperbenzoic acid. The organophosphorus compounds were obtained by a reaction sequence consisting of catalytic cycloalumination of symmetrical acetylenes with triethylaluminum in the presence of bis(cyclopentadienyl)zirconium(IV) dichloride catalyst leading to the formation of 2,3-disubstituted aluminacyclopent-2-enes and in situ reaction of the latter with dichlorophenylphosphine.
Keywordsaluminacyclopentenes 2,3-dihydrophospholes epoxyphospholanes heterocyclic compounds organoaluminum compounds zirconocene dichloride cycloalumination epoxidation metal complex catalysis
This work received financial support from the Russian Foundation for Basic Research (project 16-33-00193) and grant of the President of the Russian Federation (NSh-5240.2018.3). The structural studies were performed with the use of Collective Usage Center “Agidel” at the Institute of Petrochemistry and Catalysis, Russian Academy of Sciences.
- 1.Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. USA 1985, 82, 7096.Google Scholar
- 5.Seto, H.; Kuzuyama,T. Nat. Prod. Rep. 1999, 16, 589.Google Scholar
- 10.D'yakonov, V. A.; Makhamatkhanova, A. L.; Agliullina, R. A.; Dilmukhametova, L. K.; Tyumkina, T. V.; Dzhemilev, U. M. Beilstein J. Org. Chem. 2016, 12, 406.Google Scholar
- 12.Ito, S.; Yamashita, M.; Niimi, T.; Fujie, M.; Reddy, V. K.; Totsuka, H.; Haritha, B.; Maddali, K.; Nakamura, S.; Asai, K.; Suyama, T.; Yamashita, J.; Iguchi, Y.; Yu, G.; Oshikawa, T. Heterocycl. Commun. 2009, 15, 23.Google Scholar
- 14.Quin, L. D.; Wu, X.-P. Heteroat. Chem. 1991, 2, 359.Google Scholar