35618-58-7

Basic information

• Product Name: tricyclo[4.1.0.0~2,7~]hept-3-ene
• CAS NO: 35618-58-7
• Molecular Formula: C₇H₈
• Molecular Weight: 92.1384
• Mol File: 35618-58-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 107.4°C at 760 mmHg
• Density: 1.158g/cm³
• Vapor Pressure: 31.7mmHg at 25°C
• Refractive Index: 1.621
• CAS DataBase Reference: tricyclo[4.1.0.0~2,7~]hept-3-ene(CAS DataBase Reference)
• NIST Chemistry Reference: tricyclo[4.1.0.0~2,7~]hept-3-ene(35618-58-7)
• EPA Substance Registry System: tricyclo[4.1.0.0~2,7~]hept-3-ene(35618-58-7)

Safety Data

• Hazardous Substances Data: 35618-58-7(Hazardous Substances Data)

Upstream product

• 52911-87-2 4,5-Dibromtricyclo<4.1.0.0^2,7>hept-3-en 
• 102870-41-7 endo-6,syn-7-Dibrom-3,4-dichlorbicyclo<3.1.1>hept-2-en 
• 52911-88-3 4,5-dichlorotricyclo<4.1.0.0^2,7>hept-3-ene 
• 52911-89-4 4-Bromo-tricyclo[4.1.0.0^2,7]hept-3-ene 

Downstream Products

• 124856-52-6 1,1a,1b,7,7a,7b-Hexahydro-4-phenyl-1,7-methano-3H-cyclopropa<3',4'>cyclobuta<1',2':3,4>pyrazolo<1,2-a><1,2,4>triazol-3,5(4H)-dion 
• 96866-00-1 3-(2',4'-Cyclohexadien-1'-yl)-1,1,2,2-cyclopropanetetracarbonitrile 
• 16118-23-3 tricyclo<3.2.2.0^2,4>non-6-ene-8,8,9,9-tetracarbonitrile 
• 96865-98-4 (1R,5S,8S)-Tricyclo[3.3.1.0^2,8]non-6-ene-3,3,4,4-tetracarbonitrile 
• 544-25-2 Cyclohepta-1,3,5-triene 
• 102870-42-8 endo-6,syn-7-Diiodbicyclo<3.1.1>hept-2-en 
• 73688-32-1 6-endo-Phenylthiobicyclo<3.1.1>hept-2-en 
• 102870-47-3 2-Phenylsulfanyl-bicyclo[4.1.0]hept-3-ene 
• 102870-46-2 4-Phenylsulfanyl-bicyclo[4.1.0]hept-2-ene 
• 16118-23-3 Tricyclo<3.2.2.0^2,4>non-8-ene-6,6,7,7-tetracarbonitrile 
• 96865-98-4 Tricyclo<3.3.1.0^2,8>non-6-en-3,3,4,4-tetracarbonitril 

Relevant articles and documents

Norpinenes (Bicyclohept-2-enes) from Homobenzvalenes (Tricyclo2,7>hept-3-enes)

4,5-Dibromo-(1b) and 4,5-dichlorohomobenzvalene (1c) were converted into the tetrahalonorpinenes 2b, c by elemental bromine.In the case of unsubstituted homobenzvalene (1a) the analogous reaction could be achieved in 1percent yield only by pyridinium perbromide.Treatment of 1a, b as well as of chlorohomobenzvalenyl nitrobenzoate 1d with iodine furnished the diiodonorpinenes 3a - c.However, 7,7-dibromotetracyclo2,4.03,5>heptane (4) and bromine gave the tetrabromo-trans-tricyclo2,4>heptane derivative 5. - On irradiation in the presence of thiophenol, the homobenzvalenes 1a, c, e, f were transformed into the 6-(phenylthio)norpinenes 6a - d.The hydroxyhomobenzvalenes 1g, h afforded the 6-(phenylthio)norpinenes 6e, g as major products, the configuration at C-4 of which is inverted as compared to that of 6b - d.By using 2>-1a it was shown that with respect to stereochemistry the addition of thiophenol does not proceed uniformly.Without irradiation, 1a was consumed by thiophenol rather slowly at 20 deg C with formation of the norcarene derivatives 9 and 10 in addition to 6a. - By treatment with LiAlH4 the dichloro compound 6b gave the monochloro derivative 6h.Both 6b and 6h, however the latter one with a better yield, were converted into unsubstituted norpinene (11a) by means of sodium in liquid ammonia, thus providing a new and preparatively useful synthesis for 11a.Analogously, 6c, d furnished 4-phenylnorpinene (11b).The reaction of norpinenes 3a and 11a with N-bromosuccinimide produced the allylbromides 3d and 11c, respectively. - 13C NMR spectra of the 4-substituted norpinenes revealed a diagnostically important γ-anti-substituent effect.