Table 1.
Reduction to addition ratio for photoreaction of 5 with various nucleophiles.
| Nucleophiles | Product Ratiosa,b | |
|---|---|---|
| Reduction | Substitution (8)c | |
| MeOH | 10 (2) | 90 (98) |
| i-PrOH | 5 (4) | 95 (96) [7:8 = 4:92] |
| n-BuOH | 7 (5) | 93 (95) |
| t-BuOH | (14) | (86) |
| HOCH2CO2CH3 | − (100) | − (0) |
| HOCH(CH3)CO2C2H5 | 100 (100) | 0 (0) |
| 1,4-HOC6H4OH | 100 (100) | 0 (0) |
| (CH3)2NH2+Cl− | 10 (5) | 90 (95) |
| C6H5OH | 3 (2) | 97 (98) |
a
Determined by mass spectrometry of photoproducts from laser transient studies.
b
Determined from preparative runs using a Rayonet Photochemical Reactor in parentheses.
c
All substitution products are 2-substituted (8) rather than 6-substituted (7) unless noted otherwise