Table 1.
Stability profiles of dansylates formed from commercially-available alcohols.
| Dansylate | NaIa | Piperidineb | NaN3c | Fe(0)d | NaOHe | HBrf | BBr3g |
|---|---|---|---|---|---|---|---|
| nBu (1) | − | − | + | o | − | o | |
| iPr (2) | − | − | o | − | − | − | |
| iBu (3) | − | − | + | o | − | − | |
| Neo (4) | + | + | o | + | + | − | − |
| TCE (5) | + | R | R | − | − | + | + |
| THPM (6) | − | o | + | + | − | R | |
| Ph (7) | + | + | + | + | − | + | + |
| DFE (8) | − | − | + | − | o | + | |
| TFE (9) | + | + | o | + | − | + | + |
| HFIP (10) | + | R | R | + | − | + | + |
| TFMB (11) | + | + | − | + | − | − | − |
| Oxetane (12) | − | − | + | − | R | R |
For each condition, the dansylate was assessed to be stable (+), give partial cleavage (o), complete cleavage (−), or react to form other products (R).
a
1M NaI in acetone, reflux, 16h;
b
20% piperidine/DMF, rt, 16h;
c
0.3 mmol/ml NaN3 in DMSO, 70°C, 16h;
d
excess Fe(0), 2:2:1 EtOH:HOAc:H2O, 50°C, 1h;
e
9:1 CH2Cl2/2 M NaOH in MeOH, rt, 16h;
f
48% HBr, reflux, 2h;
g
0.1M BBr3 in CH2Cl2, rt, 2h.