16177-46-1

Basic information

• Product Name: cis-1,2-Divinylcyclobutane.
• Synonyms: cis-1,2-Divinylcyclobutane.
• CAS NO: 16177-46-1
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.18088
• Mol File: 16177-46-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 137.85°C (rough estimate)
• Flash Point: 7.3°C
• Appearance: /
• Density: 0.8010
• Vapor Pressure: 24.3mmHg at 25°C
• Refractive Index: 1.4563
• CAS DataBase Reference: cis-1,2-Divinylcyclobutane.(CAS DataBase Reference)
• NIST Chemistry Reference: cis-1,2-Divinylcyclobutane.(16177-46-1)
• EPA Substance Registry System: cis-1,2-Divinylcyclobutane.(16177-46-1)

Safety Data

• Hazardous Substances Data: 16177-46-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12/c1-3-7-5-6-8(7)4-2/h3-4,7-8H,1-2,5-6H2

Upstream product

• 106-99-0 buta-1,3-diene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 5259-71-2 (Z,E)-1,5-cyclooctadiene 
• 28636-10-4 syn-Tricyclo<4.2.0.0^2,5>octan 
• 13027-75-3 anti-tricyclo<4,2,0,0^2,5>octane 
• 25863-08-5 7,8-Diazatricyclo<4.2.2.0^2,5>dec-7-en 
• 689-97-4 3-buten-1-yne 

Downstream Products

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 1124-13-6 cis-cyclobutane-1,2-dicarboxylic acid 
• 61141-50-2 cis-1,2-Diethylcyclobutan 
• 5259-71-2 (Z,E)-1,5-cyclooctadiene 
• 53356-65-3 cis-1,2-Di-1-propinylcyclobutan 

Relevant articles and documents

Alkynes and Cumulenes, XVII, Photoaddition of Vinylacetylene to other Unsaturated Hydrocarbons

On irradiation in the presence of triplet sensitizers, vinylacetylene (1) may be added with its double bond to olefins , dienes , allenes , and diynes .The resulting multifunctionalized cyclobutane derivatives are characterized by spectroscopic and chemical methods.Since the ethinyl group of these codimers may be hydrated to the acetyl function, 1 represents a photochemical equivalent of methyl vinyl ketone which itself does not undergo the described photoadditions.When benzene (56) is employed as addition partner the primary product of the codimerisation, 54, isomerizes to vinylcyclooctatetraene (55).

Photochemistry of Alkenes. 6. Direct Irradiation of 1,5-Hexadienes: and Sigmatropic Allyl Shifts

The photochemical behavior of a series of alkyl-substituted 1,5-hexadienes has been studied.Competing allylcyclopropane formation and rearrangement to an isomeric 1,5-hexadiene via competing and sigmatropic allyl shifts, respectively, were observed.In one case a product (30 from 27) and in another a product (35 from 31) was obtained, but only in low yield.Extensive cis trans isomerization competed with the allyl shifts, and, in addition, other products were obtained which are characteristic of the photochemical behavior of isolated double bonds.At low conversion diene 10t underwent stereoselective rearrangement to 8t and 11t, whereas the cis isomer 10c afforded mixtures of the cis and trans isomers of 8 and 11.Attempts to induce the allyl migrations by sensitization with p-xylene or by irradiation at 254 nm afforded only cis trans isomerization.It is concluded that the allyl migrations occur via an excited state involving interaction between the double bonds and requiring a conformation in which the central C3-C4 bond is in a plane orthogonal to both double bonds, as proposed previously.In contrast with the acyclic dienes, 1,5-cyclooctadiene (50) afforded products 51-53 from competing , , and allyl shifts, respectively.The divergent behavior in this case apparently arises because appropriate interaction between the two double bonds can occur only in the boat conformation.