TRI-p-METHANE REARRANGEMENT

Staff:

Vladimír Církva, Stanislav Relich, Lenka Slavětínská, Leona Vlková

External co-workers:

Howard E. Zimmerman (University of Wisconsin-Madison, Chemistry Department); Jaroslav Kvíčala (Institute of Chemical Technology (ICT) Prague, Department of organic chemistry)

 

 

 

Financing, funding:

 

 

 

What is tri-p-methane rearrangement?

 

 Photochemical reaction of 3-vinyl-1,4-dienes leading to 3-vinyl cyclopentenes:

 

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Solved problematics:

 

Fundamental research on tri-p-methane rearrangement

 

Effect of substituents on regioselectivity of tri-p-methane rearrangement

 

Quantum-chemical calculations on tri-p-methane rearrangement

 

 

Publications:

[1] Zimmerman, H.E.; Církva, V.: Org. Lett. 2 (2000) 2365-2367. The tri-p-methane rearrangement: Mechanistic and exploratory organic photochemistry.

[2] Zimmerman, H.E.; Církva, V.; Jiang, L.: Tetrahedron Lett. 41 (2000) 9585-9587. A ground state Tri-p-methane rearrangement.

[3] Zimmerman, H.E.; Církva, V.: J. Org. Chem. 66 (2001) 1839-1851 and supporting inf. Excited- and ground-state versions of the Tri-p-methane rearrangement: Mechanistic and exploratory organic photochemistry.

[4] Církva, V., Zimmerman H.E.: Chem. Listy 95 (2001) 746-747. Tri-p-methanový přesmyk. (Tri-p-methane rearrangement).

[5] Zimmerman, H.E.; Novak, T.: J. Org. Chem. 68 (2003) 5056-5066. Regioselectivity of the tri-p-methane rearrangement: Mechanistic and exploratory organic photochemistry.

 

 

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