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.