Table 1. Results of the reaction of 5a–c with 2 M ammonia and 2 M ethylamine in methanol at 20°C.
Substrate | 2 M NH3 in MeOHa | 2 M EtNH2 in MeOHa | ||||
---|---|---|---|---|---|---|
t | Complete solvolysis | Product formedb | t | Complete solvolysis | Product formedb | |
5a | 7 days | ND | 2 | 1 day | 5 days | 6b |
5b | 1 day | 5 days | 2 | 5 h | 25 h | 2 + 6bc |
5c | 4 h | 20 h | 2 | 50 min | 4 h | 2 + 6bd |
aThe reagent was used in at least 10-fold excess.
bStructure of the products formed are given in Scheme 1.
cRatio 1:4.
dRatio 1:1.