The Cloke–Wilson rearrangement of aroyl-substituted donor–acceptor cylopropanes containing arylethyl donors

Abstract

The chemistry of donor-acceptor (D-A) cyclopropanes containing alkyl donors has been scantly investigated. In the present work, we have syntheszied new D-A cyclopropanes containing arylethyl donors and explored their reactivity...

Synthesis of 1-aryl-2,3-diaroyl cyclopropanes from 1,3,5-triaryl-1,5-diketones and their transformation into E,E-1,4-diaryl-1,3-butadienes

“…1 The inherent angle and torsional strains in the three-carbon ring system coupled with the presence of push–pull groups in adjacent positions bestow them with high reactivity. Such cyclopropanes undergo various transformations such as annulation, 2 rearrangement 3 and ring-opening 4 reactions upon exposure to suitable reagents to yield a diverse range of products. Most of the methods used for the synthesis of donor–acceptor cyclopropanes fall into two major categories: ( 1 ) [2 + 1] cycloaddition of carbenes generated from diazo compounds or iodonium ylides to alkenes and ( 2 ) Michael-initiated ring closure strategy involving addition of nucleophiles to electrophilic alkenes followed by cyclization.…”

SnCl4-mediated one-pot synthesis of 2,4,5-trisubstituted thiazoles from nitro-substituted donor–acceptor cyclopropanes and thioamides

“…The popularity of donor–acceptor cyclopropanes (DACs) as building blocks in organic synthesis has increased dramatically in the past two decades. 1 Their signature reactions such as annulation, 2 ring-opening 3 and rearrangement 4 reactions have provided access to numerous carbocyclic and heterocyclic compounds. The advantages of synthetic methodologies developed from DACs include easy accessibility of the starting materials, operational simplicity of the reactions and formation of the products with high yield and selectivity.…”

Formal insertion of selenoketenes into donor–acceptor cyclopropanes: mesomeric alkynylselenolates as key starting materials

“…The push–pull trigger caused by the electron-releasing donor moiety and the electron-withdrawing acceptor moiety enables the three-membered ring to behave as a masked 1,3-zwitterionic intermediate. Thus, these strained ring systems display various reactivities such as (3 + n)-cycloadditions, 3 rearrangements 4 and ring-opening reactions. 5 Highly functionalized, saturated or partially saturated four-, five-, six- or seven-membered rings are furnished by various (3 + n)-cycloaddition reactions of D–A cyclopropanes with π-systems such as carbonyls, 6 imines, 7 nitrosoarenes, 8 nitrones 9 and polarized hetero-2π-components.…”