30294-54-3

Usage

Uses

Used in Organic Chemistry Research:
1,2-dihydropentalene is used as a reactive intermediate for the study of chemical reactions and the development of new synthetic methods. Its high reactivity makes it a valuable tool in organic chemistry, allowing researchers to explore various reaction pathways and mechanisms.
Used in Pharmaceutical Development:
1,2-dihydropentalene is used as a building block in the synthesis of complex organic molecules, which can be further utilized in the development of new pharmaceuticals. Its potential in creating novel compounds with unique properties makes it a promising candidate for drug discovery and medicinal chemistry.
Used in Material Science:
1,2-dihydropentalene is used as a precursor in the development of new materials. Its structural properties and reactivity can contribute to the creation of advanced materials with specific characteristics for various applications in industries such as electronics, plastics, and coatings.

Upstream product

• 35434-64-1 tetracyclo<3.3.0.0^2,4.0^3,6>oct-7-ene 
• 694-87-1 benzocyclobutene 
• 33284-11-6 1,5-dihydropentalene 
• 83720-07-4 1,6-Cyclooctadien-3-in 
• 692-50-2 hexafluoro-2-butyne 
• 629-20-9 1,3,5,7-cyclooctatetraene 
• 2481-72-3 6-(2'-(dimethylamino)vinyl)pentafulvene 
• 29185-91-9 tetracyclo<3.3.0^2,4.0^3,6>octane 
• 30294-52-1 3-(dimethylamino)-1,2-dihydropentalene 

Downstream Products

• 108593-26-6 Tricyclo<5.3.0.0^2,5>deca-1(10),6-dien-3,3,4,4-tetracarbonitril 
• 108594-11-2 1-tert-Butyl-1,2,3,4-tetrahydropentalen 
• 108594-10-1 3-tert-Butyl-1,2,3,4-tetrahydropentalen 
• 108594-12-3 1-tert-Butyl-1,2,3,5-tetrahydropentalen 
• 100-42-5 styrene 
• 61771-84-4 1,4-dihydropentalene 
• 33284-11-6 1,5-dihydropentalene 
• 108593-21-1 1-Vinylfulven 
• 89654-25-1 1,6-Dihydropentalen 
• 116026-90-5 4-Phenyl-4-azatetracyclo<5.4.2.0^1,8.0^2,6>trideca-8,12-dien-3,5-dion 
• 116026-92-7 Hexacyclo<13.3.2.1^3,11.1^4,9.0^2,10.0^10,14>docosa-5,7,11(21),16,19-pentaen-18,22-dion 
• 116026-91-6 Hexacyclo<12.3.2.1^2,9.1^2,13.1^3,8.0^10,21>docosa-4,6,10(21),15,18-pentaen-17,22-dion 
• 116026-89-2 1,10,11,12-Tetraphenyltetracyclo<8.2.1.0^2,9.0^3,7>trideca-3,7,11-trien-13-on 
• 176714-85-5 1-bromo-1,2-dihydropentalene 

Relevant academic research and scientific papers

PHOTOCHEMISTRY OF BENZOCYCLOBUTENE

Photolysis of benzocyclobutene (1) in pentane solution at 254 nm yields 1,2-dihydropentalene (2) and 1,5-dihydropentalene (3) as the major isomeric products; formation of 2 and 3 is consistent with a "prebenzvalene"-carbene rearrangement mechanism.

A Simple Preparation of 1,2-Dihydropentalene from Cyclooctatetraene

Flash thermolysis of cyclooctatetraene leads to a mixture of four isomeric dihydropentalenes 1,3,4 and 5.Catalytic hydrogen transfer on basic alumina or silica gel furnishes pure 1,2-dihydropentalene (1).

New Pathways to Precursors of Pentalene

Pentalene dimers 2 and 3 are easily available in moderate yields by CuCl2-induced oxidative coupling of dilithium-pentalenediide (5) (Scheme 1).On the other hand, NBS bromination of 1,5-dihydropentalene (4) or of 1,2-dihydropentalene (8) gives unstable 1-bromo-1,2-dihydropentalene (9), while subsequent in-situ elimination with Et3N exclusively gives syn-cis-pentalene dimer 2 in moderale yields (Scheme3).NMR-Spectroscopic evidence for compounds 2. 3. and 9 is presented, and mechanistic alternatives for the formation of pentalene dimers 2 and 3 are discussed.

Dihydropentalenes

Applying the MNDO method the enthalpies of formation and the frontier orbitals of the six isomeric dihydropentalenes 1-6 have been calculated .An easy preparative access for the energy lower systems 1-4 is provided by the thermolysis of cyclooctatetraene (8) performed under different conditions and by different workup 1-4 were characterized by 1H- and 13C-NMR spectroscopy.

MECHANISM OF THE THERMAL CONVERSION OF TETRACYCLO(3.3.0.02,4.03.6)OCT-7-ENE INTO DIHYDROPENTALENES

One of a number of possible mechanisms has been established for the title reaction.

The Thermolysis of Tetracyclo2,4.03,6>oct-7-ene, a New Entry into (CH)8 Systems

At 270-500 deg C tetracyclo2,4.03,6>oct-7-ene is converted into equilibrating dihydropentalenes within 1-2 s.