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

Chatla Narayana, Seetharamaiyer Padmanabhan, George Kabalka

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

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 acetic acid was reported.1 This prompted us to report our results on the cleavage of ethers and regeneration of aldehydes from geminal diacetates using the boron triiodide-N,N-diethylaniline reagent.

Original languageEnglish (US)
Pages (from-to)6977-6978
Number of pages2
JournalTetrahedron Letters
Volume31
Issue number48
DOIs
StatePublished - Jan 1 1990
Externally publishedYes

Fingerprint

Boron
Ethers
Aldehydes
Boranes
Iodides
Acetic Acid
Iodine
Regeneration
Derivatives
N,N-diethylaniline

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Cleavage of ethers and geminal diacetates using the boron triiodide-N,N-diethylaniline complex. / Narayana, Chatla; Padmanabhan, Seetharamaiyer; Kabalka, George.

In: Tetrahedron Letters, Vol. 31, No. 48, 01.01.1990, p. 6977-6978.

Research output: Contribution to journalArticle

Narayana, Chatla ; Padmanabhan, Seetharamaiyer ; Kabalka, George. / Cleavage of ethers and geminal diacetates using the boron triiodide-N,N-diethylaniline complex. In: Tetrahedron Letters. 1990 ; Vol. 31, No. 48. pp. 6977-6978.
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