2,3-Dimethylenebicyclo[2.2.1]heptane Singlet oxygen

Clennan, E.L.; Matusuno, K.
J. Org. Chem. 52, 3483-3485 (1987)

Reaction: 2,3-Dimethylenebicyclo[2.2.1]heptane + ¹O₂^* ® products and/or physical quenching
Solvent: CD₃COCD₃

k = 3.6 × 10⁵(L mol^-1 s^-1), T = 195K

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements using indicator

Photosensitizer = Rose Bengal dianion; Indicator = 1,3-Diphenylisobenzofuran; k_d not given. [O₂] = O₂.

Hagenbuch, J.-P.; Birbaum, J.-L.; Metral, J.-L.; Vogel, P.
Helv. Chim. Acta 65, 887-895 (1982)

Reaction: 2,3-Dimethylenebicyclo[2.2.1]heptane + ¹O₂^* ® products
Reference Reaction: 5,6-Dimethylidene-2-bicyclo[2.2.1]heptene + ¹O₂^* ®
Solvent: Methylene chloride

k/k_reference = 8.3
T = 253K

Experimental method: Photolysis
Analytical method: nuclear magnetic resonance
Data type: Relative value measured by steady state method

Photosensitizer = 5,10,15,20-Tetraphenylporphine. Meas. k/k_ref = 8.3.

Hagenbuch, J.-P.; Birbaum, J.-L.; Metral, J.-L.; Vogel, P.
Helv. Chim. Acta 65, 887-895 (1982)

Reaction: 2,3-Dimethylenebicyclo[2.2.1]heptane + ¹O₂^* ® products
Reference Reaction: CPD + ¹O₂^* ®
Solvent: Methylene chloride

k/k_reference = < 1 × 10^-1
T = 253K

Experimental method: Photolysis
Analytical method: nuclear magnetic resonance
Data type: Relative value measured by steady state method

Photosensitizer = 5,10,15,20-Tetraphenylporphine. Meas. k/k_ref = <0.1.

Hagenbuch, J.-P.; Birbaum, J.-L.; Metral, J.-L.; Vogel, P.
Helv. Chim. Acta 65, 887-895 (1982)

Reaction: 2,3-Dimethylenebicyclo[2.2.1]heptane + ¹O₂^* ® products
Reference Reaction: 2,3-Dimethylidene-7-oxabicyclo[2.2.1]heptane + ¹O₂^* ®
Solvent: Methylene chloride

k/k_reference = 10
T = 253K

Experimental method: Photolysis
Analytical method: nuclear magnetic resonance
Data type: Relative value measured by steady state method

Photosensitizer = 5,10,15,20-Tetraphenylporphine. Meas. k/k_ref = 10.

Hagenbuch, J.-P.; Birbaum, J.-L.; Metral, J.-L.; Vogel, P.
Helv. Chim. Acta 65, 887-895 (1982)

Reaction: 2,3-Dimethylenebicyclo[2.2.1]heptane + ¹O₂^* ® products
Reference Reaction: 2,3,5,6-Tetramethylidene-7-oxabicyclo[2.2.1]heptane + ¹O₂^* ®
Solvent: Methylene chloride

k/k_reference = 50
T = 253K

Experimental method: Photolysis
Analytical method: nuclear magnetic resonance
Data type: Relative value measured by steady state method

Photosensitizer = 5,10,15,20-Tetraphenylporphine. Meas. k/k_ref = 50.

Hagenbuch, J.-P.; Birbaum, J.-L.; Metral, J.-L.; Vogel, P.
Helv. Chim. Acta 65, 887-895 (1982)

Reaction: 2,3-Dimethylenebicyclo[2.2.1]heptane + ¹O₂^* ® products
Reference Reaction: 5,6-Dimethylidene-7-oxa-2-bicyclo[2.2.1]heptene + ¹O₂^* ®
Solvent: Methylene chloride

k/k_reference = > 1 × 10³
T = 253K

Experimental method: Photolysis
Analytical method: nuclear magnetic resonance
Data type: Limiting value

Photosensitizer = 5,10,15,20-Tetraphenylporphine. Meas. k/k_ref = >1000.

Hagenbuch, J.-P.; Birbaum, J.-L.; Metral, J.-L.; Vogel, P.
Helv. Chim. Acta 65, 887-895 (1982)

Reaction: 2,3-Dimethylenebicyclo[2.2.1]heptane + ¹O₂^* ® products
Reference Reaction: 2,3,5,6-Tetramethylidene-7-oxa-2-bicyclo[2.2.1]heptane monoendoperoxide + ¹O₂^* ®
Solvent: Methylene chloride

k/k_reference = > 1 × 10³
T = 253K

Experimental method: Photolysis
Analytical method: nuclear magnetic resonance
Data type: Limiting value

Photosensitizer = 5,10,15,20-Tetraphenylporphine. Meas. k/k_ref = >1000.