1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene

Base Information

• Chemical Name: 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene
• CAS No.: 3725-33-5
• Molecular Formula: C8H10
• Molecular Weight: 106.165
• Mol file: 3725-33-5.mol

Synonyms:Tricyclo<3.3.0.0>octan;Tricyclo<5.1.0.04,8>oct-2-en;Tricyclo<3.3.0.02.6>octan;dihydrosemibullvalene;tricyclo<3.3.0.04,6>oct-2-ene;Tricyclo<3.2.1.02.8>oct-3-en;tricyclo<3,3,0,02,6>octane;

Chemical Property of 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene

Chemical Property:

• Vapor Pressure: 9.67mmHg at 25°C
• Boiling Point: 135.2°Cat760mmHg
• Flash Point: 16.1°C
• PSA: 0.00000
• Density: 1.091g/cm³
• LogP: 1.82840

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene

There total 23 articles about 1,2,2a,2b,4a,4b-hexahydrocyclopropa[cd]pentalene 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: 71.0%

rel-(1′R,2r,2′R,4′S,5R,5′S)-5-methoxy-5-methylspiro[2,5-dihydro-1,3,4-oxadiazole-2,8′-tricyclo[3.2.1.02,4]octane] → tetracyclo[3.3.0.02,8.04,6]octane + (1S,2S,5S,8R)-(-)-Tricyclo<3.3.0.02,8>oct-3-en (3725-33-5,89757-40-4,89757-48-2,142320-88-5)

Guidance literature:

In cyclohexene; at 165 ℃;

DOI:10.1021/jo4004579

Reference yield: 71.0%

rel-(1′R,2s,2′R,4′S,5R,5′S)-5-methoxy-5-methylspiro[2,5-dihydro-1,3,4-oxadiazole-2,8′-tricyclo[3.2.1.02,4]octane] → tetracyclo[3.3.0.02,8.04,6]octane + (1S,2S,5S,8R)-(-)-Tricyclo<3.3.0.02,8>oct-3-en (3725-33-5,89757-40-4,89757-48-2,142320-88-5)

Guidance literature:

In cyclohexene; at 165 ℃;

DOI:10.1021/jo4004579

Reference yield: 51.0%

(+/-)-Tricyclo<3.3.0.02,8>octan-3-on-p-tolylsulfonylhydrazon (52898-46-1,142433-80-5) → (+/-)-Tricyclo<3.3.0.02,8>oct-3-en (3725-33-5,89757-40-4,89757-48-2)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; methyllithium; In diethyl ether; 1) -15 deg C, 2 h, 2) room temperature, 16 h;

upstream raw materials:

ethene

benzene

tricyclo<5.1.0.0^2,8>oct-3-ene

5,6-Diazatricyclo<5.3.0.0^4,8>deca-2,5-dien

Downstream raw materials:

C₁₅H₁₈N₂O₂S

bicyclo[2.2.2]octan-2-ol

Refernces

PERICYCLIC TRANSFORMATIONS OF TETRACYCLO<8,2,1,0^2,90^3,8>TRIDECA-4,6,11-TRIENES, AND FORMATION OF DIHYDROSEMIBULLVALENES BY THERMAL INTRAMOLECULAR<_?4_a+_?2_a>CYCLOADDITION IN SUBSTITUTED CYCLOOCTATRIENES

10.1016/0040-4020(80)88028-8

The research focuses on the pericyclic transformations of tetracyclo[8,2,1,02'9]trideca-4,6,11-trienes, exploring the synthesis and properties of homologous and related polycyclic systems with unsaturated rings fused syn and anti to the cyclobutane moiety. The study aims to understand the thermal intramolecular [4+2] cycloaddition in substituted cyclooctatrienes, leading to the formation of dihydrosemibullvalene derivatives through a novel sequence involving cheletropic loss of carbon monoxide and electrocyclic ring opening. The conclusions drawn from the research highlight the potential for these compounds to undergo various pericyclic transformations, such as electrocyclic ring-opening and closure, and sigmatropic group transfer, which are competitive processes when steric inhibition is not severe.

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