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:

98% ^*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-chloro-3-(2-chloroethyl)benzene

3-(2-tert-butoxyethyl)chlorobenzene

1-Chloro-3-(2-isopropoxy-ethyl)-benzene

Refernces

• 1、 Nefedov, Oleg M.,Zuev, Petr S.,Maltsev, Andrey K.,Tomilov, Yuri V.. "DIRECT IR-SPECTROSCOPIC OBSERVATION OF (1+2)-CYCLOADDITION OF CYCLOPENTADIENYLIDENE TO ETHYLENE IN ARGON MATRIX". . p. 763 - 764. Retrieved 2007/10/02.
• 2、 Burger, Ulrich,Gandillon, Gerard,Mareda, Jiri. "The Ring Closure of Cyclopenta-1,3-dien-5-yl-carbene to Benzvalene. A Mechanistic Study of an Unusual Carbene Reaction". . p. 844 - 853. Retrieved 2007/10/02.