bicyclo(3.1.0)hexane

Base Information

• Chemical Name: bicyclo(3.1.0)hexane
• CAS No.: 285-58-5
• Molecular Formula: C6H10
• Molecular Weight: 82.1454
• Hs Code.: 2902199090
• Mol file: 285-58-5.mol

Synonyms:Norsabinane;Northujane

Chemical Property of bicyclo(3.1.0)hexane

Chemical Property:

• Vapor Pressure: 87.6mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Boiling Point: 82.4°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 0.939g/cm³
• LogP: 1.80640

Purity/Quality:

97% ^*data from raw suppliers

Bicyclo[3.1.0]hexane ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Bicyclo(3.1.0)hexane (also known as norsabinane or northujane) is a bicyclic hydrocarbon whose reactivity in electrophilic cleavage, such as acetolysis, is primarily governed by electronic factors like bond polarization and ionization potentials rather than ring strain. The study suggests that the polarization of the central C-C bond, influenced by orbital energy gaps, plays a critical role in determining its reactivity, emphasizing the significance of electronic over structural effects in such reactions.

Technology Process of bicyclo(3.1.0)hexane

There total 8 articles about bicyclo(3.1.0)hexane 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: 73.0%

C12H13NO2S → bicyclo<3.1.0>hexane (285-58-5) + 3-methyl-1-cyclopentene (1120-62-3) + cyclohexene (110-83-8)

Guidance literature:

With thiophenol; Irradiation;

DOI:10.1002/anie.200603282

Reference yield: 68.0%

1,3-dibromocyclohexane (3725-17-5) → bicyclo[3.1.0]hexane (285-58-5) + cyclohexa-1,3-diene (1165952-91-9) + cyclohexene (110-83-8)

Guidance literature:

With tetra-n-propylammonium bromide; In N,N-dimethyl-formamide; electrolytic reduction: platinum electrodes; reference: Ag wire. cathode and anode separated by a membrane;

Reference yield: 19.0%

trans-1,3-bis(methansulfonyloxy)cyclohexan (39967-13-0,39967-14-1,97840-76-1) → bicyclo[3.1.0]hexane (285-58-5) + cyclohexa-1,3-diene (1165952-91-9) + cyclohexene (110-83-8)

Guidance literature:

With tetra-n-propylammonium bromide; In N,N-dimethyl-formamide; electrochemical reduction (Pt-electrode);

upstream raw materials:

1,3-dibromocyclohexane

(E/Z)-1-Chloro-6-iodo-1-hexene

cis-1,3-bis(methansulfonyloxy)cyclohexan

trans-1,3-bis(methansulfonyloxy)cyclohexan

Downstream raw materials:

3-methoxycyclohexene

cyclohex-3-enyl-methyl ether

cis-1,3-dimethoxycyclohexane

DL-trans-1,3-Dimethoxycyclohexan

Refernces

Electrophilic Cleavage of Cyclopropanes. Acetolysis of Bicyclic and Tricyclic Cyclopropanes

10.1021/ja00290a042

The research investigates the acetolysis of a series of bicyclo[n.1.0]alkanes and [n.m.1]propellanes to understand the factors influencing the rates and products of these reactions. The study aims to determine the role of ring strain, ionization potentials, and bond polarization in the acetolysis process. Key chemicals used include various cyclopropane derivatives such as bicyclo[3.1.0]hexane, [3.2.1]propellane, and [4.2.1]propellane, with acetic acid serving as the solvent and p-toluenesulfonic acid as the catalyst. The researchers found that, contrary to expectations, strain energy relief has little correlation with reaction rates, while ionization potentials show a rough correlation. The degree of C-C bond polarization in the presence of a proton is a significant factor controlling the acetolysis rates. The study concludes that polarization of the central bond, influenced by the energy gap between occupied and unoccupied orbitals, is crucial for the reactivity of cyclopropanes. This finding highlights the importance of electronic factors over structural strain in determining reaction outcomes.