Abstract

The photochemistry of the derivatives of o-nitrobenzylcarboxyl esters or benzylsulfonyl derivatives has been well studied separately. But little attempt has been made to combine the fruits these two studies. Being photochemically active, benzylsulphonyl and intro groups should influence the reactivity of each other's, especially when the excited states are fully mixed due to the proximity of their location. The questions which should be clearly answered are; what kind of effect will be excerted to the other group, and whether these two functional groups are coupled in the course of the reaction. To answer the questions raised above, wer have synthesized two sulfonyl esters and four amides from the newly available starting material, 2-nitro-${\alpha}$-toluenesulfonyl chloride. The products identified from the exploratory solution photochemistry were cyclohexanol, phenol, cyclohexylamine, and sulfur dioxide. The results are not much different from the products originally anticipated. It has been temporarily concluded that there is little interaction between the benzyl sulfonyl group and ortho-nitro chromophore. The fact that a base (an amine) has been photochemically generated in solution photochemistry was further confirmed by and utilized in the solid phase quantitative photochemistry done on the film, so as to carry out the photochemical epoxide cure.

Keywords

• o-Nitrobenzylsulfonyl Photochemistry;
• $SO_2$ Photoextrusion;
• Photochemical Epoxide Cure

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Acknowledgement

Supported by : 한국과학재단

References

1. Photochem. v.9 Pillai, V. N.
2. Polym. Mat. Sci. Eng. v.66 Volksen, W.;Pascal, T.;Labadie, J. W.;Sanchez, M. I.
3. Polym. Mat. Sci. Eng. v.66 McKean, D. R.;Wallraff, G. M.;Volksen, W.;Hacker, N. P.;Sanchez, M. I.;Labadie, J. W.
4. J. Photochem. v.36 Schupp, H.;Wong, W. K.;Schnabel, W.
5. J. Org. Chem. v.58 Carpenter, B. K.;Hess, G. P.
6. J. Chem. Soc. Perkin Trans. v.2 Yamaoka, T.;Adachi, H.;Matsumoto, K.;Watanabe, H.;Shirosaki, T.
7. Tetrahedron Lett. v.30 Hamada, T.;Nishida, A.;Yonemitsu, O.
8. Tetrahedron Lett. Pincock, J. A.;Jurgens, A.
9. Aldrichimica Acta v.24
10. Tetrahedron Lett. Epling, G. A.;Walker, M. E.