Bicyclo[5.1.0]octa-2,5-diene

Base Information

• Chemical Name: Bicyclo[5.1.0]octa-2,5-diene
• CAS No.: 3725-20-0
• Molecular Formula: C8H10
• Molecular Weight: 106.167
• DSSTox Substance ID: DTXSID50958406
• Nikkaji Number: J13.233K
• Mol file: 3725-20-0.mol

Synonyms:bicyclo[5.1.0]octa-2,5-diene;Bicyclo(5.1.0)octa-2,5-diene;3725-20-0;DTXSID50958406;bicyclo[5.1.0]-octa-2,5-diene

Chemical Property of Bicyclo[5.1.0]octa-2,5-diene

Chemical Property:

• Vapor Pressure: 5.84mmHg at 25°C
• Boiling Point: 146.5°Cat760mmHg
• Flash Point: 20.4°C
• Density: 0.969g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 106.078250319
• Heavy Atom Count: 8
• Complexity: 126

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC2CC2C=C1

Technology Process of Bicyclo[5.1.0]octa-2,5-diene

There total 2 articles about Bicyclo[5.1.0]octa-2,5-diene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → Bicyclo<5.1.0>octa-2,4-diene (3725-38-0) + Bicyclo<5.1.0>octa-2,5-diene (3725-20-0) + Cyclohepta-1,3,5-triene (544-25-2)

Guidance literature:

With rhodium(II) trifluoroacetate dimer; at 10 ℃; for 0.0833333h; Product distribution; Mechanism; other aromatic compounds and diazoalkanes, var. rhodium based catalysts; relative reactivity of arenes;

DOI:10.1007/BF00961355

Reference yield:

diiodomethane (75-11-6) + Cyclohepta-1,3,5-triene (544-25-2) → Bicyclo<5.1.0>octa-2,4-diene (3725-38-0) + Bicyclo<5.1.0>octa-2,5-diene (3725-20-0) + anti,anti-Trishomocycloheptatriene (50510-95-7,62279-35-0,62279-36-1,62279-40-7) + anti-3,5-Bishomocycloheptatriene (6006-26-4,62211-27-2,62279-39-4)

Guidance literature:

With copper; zinc; In diethyl ether; for 30h; Further byproducts given. Yields of byproduct given; Heating;

DOI:10.1039/P29900000531

Reference yield:

Bicyclo<5.1.0>octa-2,5-diene (3725-20-0) → ethylbenzene (100-41-4,27536-89-6) + C8H10(1-)*Li(1+)

Guidance literature:

at -78 ℃;

DOI:10.1016/S0040-4039(00)80384-6

upstream raw materials:

diazomethane

benzene

diiodomethane

Cyclohepta-1,3,5-triene

Downstream raw materials:

ethylbenzene

Refernces

The cycloaddition-cycloelimination pathway to homotropilidenes - Synthesis and properties of homotropilidenes

10.1002/1099-0690(200107)2001:14<2639::aid-ejoc2639>3.0.co;2-0

This research investigates the synthesis and properties of homotropilidenes through a cycloaddition-cycloelimination pathway. The study aims to explore the effects of substituents on the Cope rearrangement rate and equilibrium positions of homotropilidenes. Key chemicals include 3,6-disubstituted 1,2,4,5-tetrazines and various cyclopropenes, which undergo [4+2] cycloadditions to form 3,4-diazanorcaradienes and subsequently tetracyclic azo compounds. Photolysis of these azo compounds yields homotropilidenes. The research concludes that substituents significantly influence the Cope rearrangement rate and equilibrium positions, with electronic and steric effects playing crucial roles. Symmetrical and unsymmetrical homotropilidenes were successfully synthesized, and their properties were characterized using techniques like NMR spectroscopy and UV/Vis spectroscopy. The findings provide valuable insights into the structure and reactivity of homotropilidenes, contributing to the understanding of pericyclic reactions and the development of new synthetic methods. In the research, homotropilidenes are described as a class of compounds with significant structural and mechanistic interest, particularly due to their involvement in the degenerate [3,3]-sigmatropic rearrangement.

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