Table 3. Synthesis, melting points and crystal habit.
| D A | D:A ratio | Solvent† | Melting point (C) | Shape/color |
|---|---|---|---|---|
| IF4-COOH2 | 1:1 | MeOH/CH2Cl2 | 125129 | Colorless blocks |
| IF4-COOH4 | 1:4 | EtOH/CH2Cl2 | 102104 | Large colorless needles |
| IF4-COOH12 | 1:1 | MeOH/trace CH2Cl2 | 165170 dec. | Colorless thin plates |
| IF4-COOH13 | 1:1 | MeOH | 138141 dec | Colorless rectangular prisms |
| IF4-COOH16 | 1:2 | EtOAc/NitroMe | 111115 | Colorless blocks |
| BrF4-COOH11 | 1:1 | Chloroform | 137139 | Off-white prisms |
| I-COOH11 | 1:1 | MeOH/EtOH | 190192 | Opaque prisms |
| I-COOH12 | 1:2 | MeOH/EtOH | 179182 | Colorless plates |
| Br-COOH2 | 1:4 | MeOH | 210221 | Colorless, flat, large plates |
| Br-COOH3 | 1:4 | EtOAc | 151153 | Colorless blocks |
| Br-COOH5 | 1:4 | EtOAc | 159162 | Colorless, short, thin needles |
| Br-COOH12 | 1:2 | MeOH | 159164 dec. | Colorless blocks |
| Br-COOH11 | 1:2 | MeOH/EtOH | 140142 | Colorless blocks |
| IF4-OX3 | 1:1 | MeOH | 9094 dec. | Yellow, wide needles |
| IF4-OX11 | 1:1 | MeOH | 135142 | Opaque, rectangular prisms |
| IF4-OX13 | 1:1 | EtOAc/NitroMe | 133135 | Colorless thin needles |
| BrF4-OX14 | 1:1 | MeOH/EtOH | 141145 | Colorless long, thin needles |
| Br-OX5 | 1:1 | MeOH | 108112 | Colorless, rectangular prisms |
| IF4-OH2 | 1:1 | MeOH | 9798 dec. | Light yellow needles |
| IF4-OH16 | 1:1 | MeOH | 102106 dec. | Large orange rectangular prism |
| BrF4-OH2 | 1:1 | MeOH | 100103 dec. | Light yellow needles |
| BrF4-OH11 | 1:1 | MeOH | 125130 | Colorless, long needles |
| BrF4-OH12 | 1:1 | MeOH | 118119 | Colorless, long, thin needles |
| BrF4-OH13 | 1:1 | MeOH | 119121 dec. | Flat colorless rectangular plate |
†
MeOH = methanol, EtOH = ethanol, CH2Cl2 = dichloromethane, EtOAc = ethyl acetate, NitroMe = nitromethane.