Synlett 2018; 29(05): 627-629
DOI: 10.1055/s-0036-1591731
letter
© Georg Thieme Verlag Stuttgart · New York

Allyl and 2-Cyclopropylethyl Rearrangements in the Reaction of 1-Alkenylaluminums with Diiodomethane/Triethylaluminum Reagent

Ilfir R. Ramazanov*
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: Ilfir.ramazanov@gmail.com
,
Alsu V. Yaroslavova
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: Ilfir.ramazanov@gmail.com
,
Niyaz R. Yaubasarov
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: Ilfir.ramazanov@gmail.com
,
Usein M. Dzhemilev
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: Ilfir.ramazanov@gmail.com
› Author Affiliations
This work was supported by the Department of Chemistry and ­Material Sciences of the Russian Academy of Sciences (program no. 1-OKhNM), the Russian Foundation for Basic Research (grant no. 16-03-00935) and by a Grant from the RF President (Sci. Sh.–6651.2016.3).
Further Information

Publication History

Received: 18 September 2017

Accepted after revision: 03 November 2017

Publication Date:
28 November 2017 (eFirst)

Abstract

The reaction of diiodomethane and triethylaluminum with substituted 1-alkenylaluminums obtained by the Zr-catalyzed carbo- or cycloalumination of mono- or dialkyl-substituted alkynes resulted in the selective formation of di- and tetrasubstituted cyclopropanes. 1-Alkenylaluminums prepared from substituted propargylamines reacted with diiodomethane and triethylaluminum to give substituted allylamines. A plausible mechanism for the reaction of the 1-alkenylaluminums with diiodomethane/triethylaluminum is proposed.

Supporting Information

 
  • References and Notes

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