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. 2002 Mar 1;30(5):1124–1131. doi: 10.1093/nar/30.5.1124

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.