Four‐Membered Cycle Formation Challenge: GaCl 3 ‐Promoted Formal [2+2]‐Cycloaddition of Donor–Acceptor Cyclopropanes to Bicyclobutylidene | Zendy

Zotova Maria A. | Zendy; Novikov Roman A. | Zendy; Volodin Alexander D. | Zendy; Korlyukov Alexander A. | Zendy; Tkachev Yaroslav V. | Zendy; Korolev Victor A. | Zendy; Tomilov Yury V. | Zendy

Premium

Four‐Membered Cycle Formation Challenge: GaCl 3 ‐Promoted Formal [2+2]‐Cycloaddition of Donor–Acceptor Cyclopropanes to Bicyclobutylidene

Author(s) -

Zotova Maria A.,

Novikov Roman A.,

Volodin Alexander D.,

Korlyukov Alexander A.,

Tkachev Yaroslav V.,

Korolev Victor A.,

Tomilov Yury V.

Publication year - 2019

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201900329

Subject(s) - chemistry , cyclobutane , cycloaddition , moiety , ring (chemistry) , propellane , acceptor , stereochemistry , bicyclic molecule , medicinal chemistry , catalysis , organic chemistry , physics , condensed matter physics

The first selective process of formal [2+2]‐cycloaddition of donor–acceptor cyclopropanes (DAC) to multiple C–C bonds to form a four‐membered ring in the product has been developed. Bicyclobutylidene is used do demonstrate this reaction. The process is promoted by GaCl 3 and occurs through generation of 1,2‐zwitterionic intermediates. A carbocationic rearrangement occurs in the bicyclobutylidene moiety. It results in expansion of both cyclobutane rings into five‐membered ones and formation of a [2.3.3]propellane skeleton in the final product.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research