[18135-48-3] · C6H15ISi · (3-Iodopropyl)trimethylsilane · (MW 242.20)
(reagent equivalent to
Physical Data: clear liquid; bp 84-86 °C/25 mmHg.
Solubility: sol hexane, THF
Handling, Storage, and Precautions: no detail has been reported. However, the usual handling for common alkyl iodides (e.g. iodohexane) may be followed.
Phosphines and amines are alkylated by the title iodide (1) to give silylpropylated compounds (eq 1).3,4
Reagent (1) serves as a
-CH2CH2CH2+ equivalent, which is illustrated in a preparation of cyclopentanones from carboxylic acids (eq 2).1,2
Thus alkylation of carboxylic acid dianions with (1) affords the 2-[3-(trimethylsilyl)propyl]alkanoic acids in good yields. After the conversion of these acids to the corresponding acyl chlorides with Oxalyl Chloride, intramolecular acylation of the alkylsilane with Aluminum Chloride affords cyclopentanones in good yields. Examples are shown in eqs 3 and 4.
A related bromide, Me3Si(CH2)3Br, is also known and may be used in a similar way.1
Tokyo Institute of Technology, Yokohama, Japan