56061-45-1

Upstream product

• 3481-02-5 cyclopropyl phenyl ketone 
• 3607-17-8 3-bromopropyltriphenylphosphonium bromide 
• 14633-95-5 triphenylphosphonium cyclopropylide 
• 14114-05-7 cyclopropyltriphenylphosphonium bromide 

Downstream Products

• 56061-52-0 1-[1-((Z)-4-Chloro-1-phenyl-but-1-enyl)-cyclopropylsulfanyl]-2,4-dinitro-benzene 
• 56061-53-1 1-[1-((E)-4-Chloro-1-phenyl-but-1-enyl)-cyclopropylsulfanyl]-2,4-dinitro-benzene 
• 142428-11-3 5,5-dichloro-6-phenyl-6-cyclopropylspiro<2,3>hexan-4-one 

Relevant academic research and scientific papers

Polylithiumorganic compounds -19. Regioselective carbon-carbon σ-bond scission followed by a 1,6-proton shift upon the reductive metalation of benzylidenecyclopropane derivatives with lithium metal

Depending on the substituent α-substituted benzylidenecyclopropanes (32) react more or less readily with lithium dust (2% sodium) in diethyl ether whereby a regioselective scission of only the cyclopropane σ-bond cis to the phenyl ring takes place. Upon raising the temperature the primarily formed 1,3-dilithiumorganic compound due to an agostic interaction rearranges by a 1,6-proton shift into a doubly bridged 1,4-dilithio compound. With α-methylbenzylidenecyclopropane (32c) this rearrangement was shown to occur intermolecularly via a trilithiumorganic compound 56. The suggested mechanism of these reductive metalation reactions via a bisected radical anion 87 where the lithium is mainly bound to the cyclopropyl carbon atom and oriented syn to the phenyl ring, was supported by MNDO (geometries) and ab initio (energies) calculations.

Biscyclopropyl titanocene: A novel reagent for the synthesis of alkylidene and vinyl cyclopropanes

Alkylidene cyclopropane derivatives are obtained by reaction of biscyclopropyl titanocene with several types of carbonyl compounds, including aldehydes, ketones and esters. In some cases the isomeric vinyl cyclopropane products are also obtained. Biscyclopropyl titanocene also reacts with alkynes forming, after acidification, the corresponding vinyl cyclopropanes.

AN EFFICIENT METHOD FOR THE PREPARATION OF ALKYLIDENECYCLOPROPANES

Yields obtained from Wittig reactions with cyclopropylidenetriphenylphosporane are greatly improved by addition of the phase-transfer catalyst, TDA-1.

METALLATION OF 1-CYCLOPROPYL-1-PHENYLMETHYLENECYCLOPROPANE

The metallation of 1-cyclopropyl-1-phenylmethylenecyclopropane takes place exclusively in the small ring with the exocyclic double bond and under milder conditions than metallation of 1-methyl-1-cyclopropyl- and 1,1-dicyclopropylmethylenecyclopropane.The