Iodination with triphenylphosphine iodine imidazole mechanism
Answers
[603-35-0] · C18H15P · Triphenylphosphine-Iodine · (MW 262.30) (I2)
[7553-56-2] · I2 · Triphenylphosphine-Iodine · (MW 253.80) (Ph3P.I2)
[80800-01-2] · C18H15I2P · Triphenylphosphine-Iodine · (MW 516.10)
(conversion of alcohols,6,7 thiols,11c and enols9 into iodides; reduction of various sulfur derivatives to sulfides or thiols;11c reduction of epoxides,13 iodohydrins,16 and vicinal diols17a to alkenes; production of iodohydrins from epoxides;14 esterification of carboxylic acids;18 acetalizations of carbonyl groups19)
Alternate Names: triphenylphosphine diiodide; iodotriphenylphosphonium iodide; diiodotriphenylphosphorane.
Physical Data: adduct:2,4 bright yellow solid (from ether). Ph3P: mp 80.5 °C; bp 377 °C (in inert gas); d254 1.194 g cm-3; d804 (liq) 1.075 g cm-3; n80D 1.6358. I2: mp 113.6 °C; bp 184.3 °C; d 4.93 g cm-3.
Solubility: Ph3P: sol ether, PhH, CHCl3, AcOH; less sol alcohol; practically insol H2O. I2: sol ether (25.2 g/100 mL), PhH (14.1 g/100 mL), alcohol (21.4 g/100 mL), MeOH (23 g/100 mL), CHCl3, CCl4; less sol H2O (0.03 g/100 mL).
Form Supplied in: the adduct is not commercially available. Ph3P: odourless monoclinic platelets or prisms; purity ~99%; typical impurity: Ph3PO ~1%. I2: bluish-black scales or plates with metallic lustre; characteristic odour; sharp, acrid taste and violet corrosive vapour; purity &egt;99.8%
Analysis of Reagent Purity: adduct.2 Ph3P and Ph3PO: 31P NMR (PhMe/MeCN, MeCN, pyridine; CCl4) -5 to -8 and +29 to +25.
Preparative Method: for synthetic purposes, the reagent is generally prepared in situ just before use, by addition of Iodine to Triphenylphosphine (or vice versa) in different solvents.
Handling, Storage, and Precautions: Ph3P: irritant; harmful; do not get in eyes, on the skin, or on clothing; avoid contact and inhalation; use with adequate ventilation; keep containers tightly closed and store in a cool dry place; incompatible with strong oxidizing agents. I2: harmful; corrosive; severe lachrymator; do no get in eyes, on the skin, or on clothing; avoid prolonged or repeated exposure; keep containers tightly closed in a cool dry place; incompatible with Mg, Zn, Al, Sb, and NH3; reacts violently with acetaldehyde. These reagents should be handled in a fume hood.
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