Spiro[2.4]hepta-4,6-diene

Base Information

• Chemical Name: Spiro[2.4]hepta-4,6-diene
• CAS No.: 765-46-8
• Molecular Formula: C7H8
• Molecular Weight: 92.1405
• Mol file: 765-46-8.mol

Synonyms:Spiroheptadiene

Chemical Property of Spiro[2.4]hepta-4,6-diene

Chemical Property:

• Vapor Pressure: 12.8mmHg at 25°C
• Refractive Index: n20/D 1.50
• Boiling Point: 128.7°C at 760 mmHg
• Flash Point: 15 °C
• PSA: 0.00000
• Density: 0.92 g/mL at 20 °C(lit.)
• LogP: 1.89260
• Storage Temp.: −20°C

Purity/Quality:

97% ^*data from raw suppliers

Spiroheptadiene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn,T
• Statements: 11-36/37/38-65-45
• Safety Statements: 26-62-45-16-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Spiroheptadiene is a chemical reagent used in the skeletal rearrangement of spirotricyclic olefins. Also used in the preparation of (phosphinyl)ethyl chelate complexes.

Technology Process of Spiro[2.4]hepta-4,6-diene

There total 7 articles about Spiro[2.4]hepta-4,6-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: 62.0%

4,4-dichlorodispiro2,7.03,5>undec-9-ene-11,1''-cyclopropane> (86301-91-9) → 1-chloro-3-(2-chloroethyl)benzene (5182-43-4) + spiro[2.4]hepta-4,6-diene (765-46-8)

Guidance literature:

at 180 - 190 ℃; Mechanism; var. cyclopropanespiro-6-(4,4-dihalogenotetracyclo<6.2.1.0^2,7.0^3,5>undec-9-ene)-11-spirocyclopropanes;

Reference yield: 47.5%

methyllithium (917-54-4) + 7,7-dibromo-2-norbornene (77333-79-0) → norborn-2-ene (498-66-8) + syn-7-bromobicyclo<2.2.1>heptene (60154-55-4) + Bicyclo<3.2.0>heptadien-1,6 (32316-40-8) + syn-7-bromo-7-methylnorbornene (14025-97-9,86970-70-9) + spiro[2.4]hepta-4,6-diene (765-46-8)

Guidance literature:

at 100 ℃; under 0.005 Torr; Product distribution; other reaction conditions;

DOI:10.1021/ja00398a052

Reference yield: 38.0%

5-chloromethyl-5-methyl-cyclopenta-1,3-diene (74130-25-9) → toluene (108-88-3,15644-74-3,16713-13-6) + 1-methylbenzvalene + spiro[2.4]hepta-4,6-diene (765-46-8)

Guidance literature:

With n-butyllithium; 18-crown-6 ether; potassium tert-butylate; In diethyl ether; for 3h; Ambient temperature;

DOI:10.1002/hlca.19810640323

upstream raw materials:

ethene

5-diazo-1,3-cyclopentadiene

5-chloromethyl-5-methyl-cyclopenta-1,3-diene

4,4-dichlorodispiro2,7.0^3,5>undec-9-ene-11,1''-cyclopropane>

Downstream raw materials:

endo-cis-2,3-Dicarboxy-bicyclo<2.2.1>hept-5-en-spiro<7>cyclopropan<1'>-anhydrid

1,1-Dimethylcyclopentane

1-chloro-3-(2-chloroethyl)benzene

endo-spiro(cyclopropane-1',8-tricyclo<3.2.1.0^2,4>oct-6-ene)

Refernces

DIELS-ALDER REACTIONS OF 1,2,3,6-TETRAHYDROBENZOCYCLOBUTENE-3,6-DIONES. A NEW SYNTHESIS OF <4.4.2>PROPELLANES AND A DIVERGENCE OF SITESELECTIVITY CONTROLLED BY STERIC HINDRANCE

10.1246/cl.1981.1547

The research investigates the Diels-Alder reactions of 1,2,3,6-tetrahydrobenzocyclobutene-3,6-diones, leading to a new synthesis of [4.4.2] propellanes and the creation of novel strained cage molecules. The study explores the site selectivity of these reactions, which is influenced by both the dienophilicity of the double bonds and steric interactions. Key chemicals involved include 1,2,3,6-tetrahydrobenzocyclobutene-3,6-dione (1) and various 1,3-dienes such as butadienes (2a-e), furan (2f), anthracene (2g), cyclopentadienones (2h-i), cyclopentadiene (2j), and spiro[2,4]hepta-4,6-diene (2k). The adducts formed from these reactions, such as internal adducts 3a-e and external adducts 4j-k, were further studied through photochemical transformations to yield strained cage molecules like compounds 9-15. The research highlights the importance of steric hindrance in controlling the site selectivity of these reactions and provides insights into the properties of the resulting cage molecules.

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