Abstract
Photochemical electrophilic aromatic substitution processes in deuterated and tritiated anisoles and toluenes have been examined. Valence isomerization did not occur in anisole on irradiation. The relative reactivities of the ortho, meta and para positions in toluene are 2:1:1·4 respectively, differing from those in the ground state. Up to 51% exchange has been observed for o-D-toluene and up to 30% exchange for o-D-anisole after 8 h irradiation. Extensive photodecomposition occurs under all conditions with anisole but is slower with toluene. Comparison of the observed substitution pattern of toluene with excited state electron distributions points to the involvement of the second excited singlet and first excited triplet states in the photochemical hydrogen exchange process.
| Original language | English |
|---|---|
| Pages (from-to) | 495-498 |
| Number of pages | 4 |
| Journal | Tetrahedron |
| Volume | 31 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 1975 |
| Externally published | Yes |