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Cleavage of ethers and geminal diacetates using the boron triiodide-N,N-diethylaniline complex

โœ Scribed by Chatla Narayana; Seetharamaiyer Padmanabhan; George W. Kabalka


Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
128 KB
Volume
31
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The boron triiodide-N,N-diethylaniline complex, generated in situ from borane:N,N-diethylaniline and iodine cleaves ethers and regenerates carbox-aldehydes from the corresponding geminal diacetate derivatives under mild conditions in good yields.

Recently a simple procedure for the preparation of alkyl and alkenyl iodides in good yields using boron triiodide-N,N-diethylaniline complex and


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Hydroiodic acid generated in situ from Bl3:N,N-diethylaniline complex and acetic acid~ readily adds to alkenes and alkynes in Markovnikov fashion to form alkyl and alkenyl iodides in good yields under mild conditions. Markovnikov addition of hydrogen halides to alkenes and alkynes is one of the mos