3725-33-5

Basic information

• Product Name: 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene
• Synonyms: Cyclopropa[cd]pentalene, 1,2,2a,2b,4a,4b-hexahydro-
• CAS NO: 3725-33-5
• Molecular Formula: C₈H₁₀
• Molecular Weight: 106.165
• Mol File: 3725-33-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 135.2°C at 760 mmHg
• Flash Point: 16.1°C
• Density: 1.091g/cm³
• Vapor Pressure: 9.67mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene(3725-33-5)
• EPA Substance Registry System: 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene(3725-33-5)

Safety Data

• Hazardous Substances Data: 3725-33-5(Hazardous Substances Data)

Usage

Chemical structure

A unique structure consisting of a cyclopropyl ring fused to a five-membered ring.

Strain

Highly strained and unstable molecule due to its ring system.

Reactivity

Potential reactivity and synthetic applications.

Interest in chemistry

Of interest in the field of organic and computational chemistry as a model for studying the reactivity and stability of highly strained compounds.

Applications

Potential applications in the development of new synthetic methodologies and as a building block for the synthesis of complex organic molecules.

Uniqueness

Its unique structure and reactivity make it a fascinating target for chemical studies and potential future applications.

Upstream product

• 74-85-1 ethene 
• 71-43-2 benzene 
• 102575-26-8 tricyclo<5.1.0.0^2,8>oct-3-ene 
• 56457-36-4 5,6-Diazatricyclo<5.3.0.0^4,8>deca-2,5-dien 
• 14224-86-3 endo-Tricyclo<3.2.1.0^2,4>octane-8-one 
• 77551-16-7 (1R,2S,5S,8S)-(+)-Tricyclo<3.3.0.0^2,8>octan-3-on 
• 89757-44-8 5,6-Diaza-tricyclo[5.3.0.0^4,8]deca-2,9-diene-5,6-dicarboxylic acid diphenyl ester 
• 89757-44-8 (1S,4S,8R)-5,6-Diaza-tricyclo[5.3.0.0^4,8]deca-2,9-diene-5,6-dicarboxylic acid diphenyl ester 
• 89757-44-8 5,6-Diaza-tricyclo[5.3.0.0^4,8]deca-2,9-diene-5,6-dicarboxylic acid diphenyl ester 
• 56457-36-4 (+)-9,10-Dihydro-5,6-diazalumibullvalene 
• 77523-29-6 tricyclo[3.3.0.0^2,8]octan-3-one 
• 103148-60-3 3,exo-7,syn-8-Tribrom-2-iodbicyclo<4.1.1>oct-3-ene 
• 103148-56-7 2,3,7,8-tetrabromobicyclo<4.1.1>oct-3-ene 
• 103148-57-8 3,exo-7,syn-8-tribromobicyclo<4.1.1>oct-2-ene 

Downstream Products

• 57374-30-8 C₁₅H₁₈N₂O₂S 
• 18684-63-4 bicyclo[2.2.2]octan-2-ol 

Relevant articles and documents

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Probing the nature and extent of stabilization within foiled carbenes: Homoallylic participation by a neighboring cyclopropane ring

Oxadiazoline 6 was synthesized to generate endo-tricyclo[3.2.1.0 2,4]octan-8-ylidene (3) by either photolysis or thermolysis. Diastereomer 6a thermally decomposed twice as fast as 6b. Carbene 3 was trapped stereoselectively by acrylonitrile and diethylamine in high yields. It behaved as a nucleophilic carbene with electron-poor alkenes, like acrylonitrile, but as an electrophile with very electron-rich species, such as diethylamine. However, when the reactions were performed in cyclohexane and cyclohexene, isomerization of 3 was favored. Replacement of the double bond in 7-norbornenylidene (1) by the single bond in the endo-fused cyclopropane unit of carbene 3 led to similar outcomes. Carbene 3 rightfully belongs to the family of foiled carbenes.

Stereochemical Course of the Denitrogenation of Optically Active 9,10-Dihydro-5,6-diazalumibullvalene to Optically Active 3,4-Dihydrosemibullvalene

Thermal decomposition of optical active diazalumibullvalene derivative (+)-6 gives optical active dihydrosemibullvalene (+)-5.The absolute configurations of optical active 6 and 5 were determined by correlation to tricyclooctanone 9 and 2-cyclopentene-1-a

DENITROGENIERUNG VON OPTISCH AKTIVEM 9,10-DIHYDRO-5,6-DIAZALUMIBULLVALEN

Thermal decomposition of optically active title compound 1 yields optically active 2.Denitrogenations of 6 and 7 lead to semibullvalenes 8 and 9 respectively as the major products.These results indicate a concerted nitrogen expulsion.