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Usage

Uses

Used in Organic Synthesis:
Cyclopropylidenecyclobutane is utilized as a reactive intermediate in organic synthesis for its high reactivity and potential to participate in unique chemical reactions. Its strained structure allows it to be a valuable building block for the creation of complex organic molecules.
Used in Materials Science:
In the field of materials science, cyclopropylidenecyclobutane is employed as a precursor for developing new materials with novel properties. Its unique structure and reactivity can contribute to the discovery of innovative materials with potential applications in various industries.
Used in Theoretical and Experimental Chemistry:
Cyclopropylidenecyclobutane serves as a subject of study in theoretical and experimental chemistry. Researchers are intrigued by its properties and reactivity, which can lead to the development of new synthetic methods and a deeper understanding of chemical reactions involving strained hydrocarbons.

Upstream product

• 20036-34-4 1-methylenespiro[2.3]hexane 
• 1191-95-3 cyclobutanone 
• 14633-95-5 triphenylphosphonium cyclopropylide 
• 14114-05-7 cyclopropyltriphenylphosphonium bromide 
• 14924-53-9 ethyl cyclobutylcarboxylate 
• 63049-05-8 spiro<3.3>heptane-1-one 
• 112650-60-9 1-cyclobutylcyclopropan-1-ol 
• 400820-18-0 1-cyclobutyl-1-(p-tolylsulfonyloxy)cyclopropane 
• 186581-53-3 diazomethane 
• 7417-52-9 1,1-trimethyleneallene 

Downstream Products

• 63049-05-8 spiro<3.3>heptane-1-one 
• 84565-29-7 1-(1-Amino-cyclobutyl)-cyclopropanol 
• 84565-28-6 5-azaspiro[3.4]octan-6-one 
• 84565-26-4 6-oxaspiro[3.4]octan-5-one 
• 400820-22-6 9-methyl-10-phenyl-8-oxa-9-azadispiro[2.0.3.3]decane 

Relevant academic research and scientific papers

Competitive 1,2-C Atom Shifts in the Strained Carbene Spiro[3.3]hept-1-ylidene Explained by Distinct Ring-Puckered Conformers

Spiro[3.3]hept-1-ylidene is a markedly strained carbene reaction intermediate that was generated by high-vacuum flash pyrolysis (HVFP) of the corresponding p-tosylhydrazone sodium salt. Five hydrocarbons were produced from the Bamford-Stevens reactant in 82% overall yield. The carbene undergoes two [1,2]-sigmatropic rearrangements via competing 1,2-C atom shifts. Ring-contraction yields cyclopropylidenecyclobutane, while ring-expansion affords bicyclo[3.2.0]hept-1(5)-ene. The ring contraction is regiospecific despite the formation of some 1-methylenespiro[2.3]hexane. It does not originate from the carbene under HVFP conditions. Instead, it comes from a methylenecyclopropane-type rearrangement of chemically activated cyclopropylidenecyclobutane. Similarly, some chemically activated bicyclo[3.2.0]hept-1(5)-ene rearranges to 1,2-dimethylenecyclopentane via electrocyclic ring-opening. Accounting for the conversion of primary products to secondary ones, relative yields indicate that ring-contraction within the carbene prevails over ring-expansion by a factor of 6.7:1. Computational chemistry was used to assess the structures, conformations, energies, strain energies, transition states, and activation energies of these rearrangements with the goal of explaining product selectivities. The dual-ringed carbene is predicted to assume four distinct geometric conformations that have a bearing on transition-state selection. The reactive cyclobutylidene units of two conformers are significantly puckered, like cyclobutylidene itself, while those of the other two are flatter. The selectivity of the title carbene is compared with that of spiro[2.3]hex-4-ylidene.

Cyclobutylidenecyclopropane: New synthesis and use in 1,3-dipolar cycloadditions - A direct route to spirocyclopropane-annulated azepinone derivatives

Cyclobutylidenecyclopropane (7) was prepared in multigram quantities by a new three-step sequence starting from ethyl cyclobutanecarboxylate (4) (39% overall yield). 1,3-Dipolar cycloadditions of phenyl- (9), pyridyl- (10), and the newly prepared (four st

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.

CYCLOPROPANATION OF ALLENES WITH DIAZOMETHANE IN THE PRESENCE OF PALLADIUM(II) COMPOUNDS

The reaction of substituted allenes with diazomethane in the presence of palladium(II) compounds takes place at the less substituted double bond with the formation of the corresponding methylenecyclopropanes.

The chemistry of small-ring compounds. Part 47. Small-ring interference in the ozonolysis of cyclopropylidenecycloalkanes

Ozonolysis of olefins Ia-c containing a cyclpropylidene group, does not follow the classical Criegee mechanism but gives the anomalous products IIa-c, IIIa-c, IVa-c, and Va-c, as outlined in Scheme 2.None of these oxidation products contains the cycloprop