1076-69-3

Basic information

• Product Name: bicyclo[6.4.0]dodeca-8,10,12-triene
• Synonyms: bicyclo[6.4.0]dodeca-8,10,12-triene;5,6,7,8,9,10-Hexahydrobenzocyclooctene;Bicyclo[6.4.0]dodecane-1(12),8,10-triene;Benzocyclooctane
• CAS NO: 1076-69-3
• Molecular Formula: C₁₂H₁₆
• Molecular Weight: 160.26
• Mol File: 1076-69-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 252.6°C at 760 mmHg
• Flash Point: 100.1°C
• Appearance: /
• Density: 0.933g/cm³
• Vapor Pressure: 0.0304mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: bicyclo[6.4.0]dodeca-8,10,12-triene(CAS DataBase Reference)
• NIST Chemistry Reference: bicyclo[6.4.0]dodeca-8,10,12-triene(1076-69-3)
• EPA Substance Registry System: bicyclo[6.4.0]dodeca-8,10,12-triene(1076-69-3)

Safety Data

• Hazardous Substances Data: 1076-69-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16/c1-2-4-8-12-10-6-5-9-11(12)7-3-1/h5-6,9-10H,1-4,7-8H2

Upstream product

• 53011-74-8 <6>-paracyclophane 
• 104509-19-5 1-Methylen-6,6-pentamethylen-cyclohexadien-(2,4) 
• 75152-10-2 (Z)-4,5-diethynyl-4-octene 
• 78071-49-5 (Z)-dodeca-4,8-diyn-6-ene 
• 107396-45-2 1,8-Dibromo-bicyclo[6.2.2]dodeca-9,11-diene 
• 64492-96-2 1,4-hexamethylene Dewar benzene 

Relevant articles and documents

Telomers of Bent Arenes. Acid-Catalyzed Dimerization and Trimerization of the 1,4-Hexamethylene-Bridged Arenes Paracyclophane, (1,4)Napthalenophane, and (1,4)Anthracenophane

Whereas treatment of 1,4-hexamethylene-bridged benzene paracyclophane (1) with a catalytic amount of H2SO4 gave, as a minor product, dimer 6, along with isomers 4 and 5, similar treatment of 1,4-hexamethylene-bridged naphthalene (1,4)naphthalenophane (2) afforded predominantly dimers 7 and 8, together with trimers 9 and 10.The 1,4-hexamethylene-bridged anthracene (1,4)anthracenophane (3) yielded only trimers 13 and 14.

Absence of Intersystem Crossing in 1,4-Didehydrobenzene

The rate of singlet-to-triplet intersystem crossing in 1,4-didehydrobenzene (the biradical produced as a reactive intermediate in the thermal cycloaromatization of enediynes), cannot be increased by the application of an external magnetic field.The rate of product formation and the distribution of stable products of 2,3-di-n-propyl-1,4-didehydrobenzene thermolysis is unchanged at magnetic flux densities in the range 0-2000 G and at 66 000 G.Similarly, the rate of thermolysis of an unsymmetrical enediyne is insensitive to magnetic field flux in the same range.This finding precludes the modulation of enediyne reaction rates in pharmaceutical and synthetic pursuits.

SYNTHESIS, STRUCTURE AND REACTIVITIES OF PARACYCLOPHANES

The synthesis, structure and reactivities of paracyclophanes 2a-c, the smallest bridged paracyclophanes so far isolated, are described.The parent hydrocarbon 2a has been efficiently synthesized by oxidative decarboxylation of propellenecarboxylic acid (7) by lead tetraacetate.The 8-carbomethoxy derivative 2b has been quantitatively synthesizedby thermal valence isomerization of the propelladiene (4b) (Dewar isomer of 2b).X-Ray structure analysis of the crystalline 2c has revealed that the benzene ring of 2c is severely deformed into a boat conformation with deformation angles of α=20.5 degree and β=18.5 degree.Furthermore, the bond angles of the bridging chain (C(2), C(3), C(4) and C(5)) are considerably expanded from the normal sp3 angle.Vapor phase thermolysis of 2a gives the spiro triene 12 via homolysis at the benzyl position.Acid-catalyzed isomerization of 2a with trifluoroacetic acid takes place readily to afford the meta and ortho isomers 13a and 14a in a ratio of 1:3.UV irradiation of the ester 2b brings about valence isomerization to the Dewar isomer 4b which izomerizes slowly to the prismane derivative 15a on further irradiation.A cycloaddition of 2a with N-phenyl-1,2,4-triazoline-3,5-dione occurs at room temperature to give mainly adduct 16.Addition of bromine to 2a takes place to furnish quantitatively the unstable 1,4-addition product 18.Oxidation of 2a with mCPBA readily takes place to give the dienone dimer 20 which affords on UV irradiation the cage diketone 21 derived from intramolecular photocycloaddition.