89796-86-1Relevant academic research and scientific papers
A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents
Janicki, Slawomir Z.,Fairgrieve, Jennifer M.,Petillo, Peter A.
, p. 3694 - 3700 (2007/10/03)
The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a 50 mmol scale.
Three Component Reactions. XII. Alkoxychlorination of 3-Chloropropene and 3-Methoxypropene
Beger, J.,Schiefer, H.
, p. 1039 - 1047 (2007/10/02)
By capillar GLC and 13C-n.m.r. spectroscopy was demonstrated, that - in contrast to the communications of other authors - both expected isomeric alkoxychlorination products are formed in the chlorination of 3-chloropropene in presence of several alkanols.Isomers with anti-Markovnikov orientation dominated in all pairs of isomers which we have identified.Analogous product relations were found in the chlorination as well as in the methoxychlorination of 3-methoxypropene.
