Fragmentation of chloroperoxides: Hypochlorite-mediated dehydration of hydroperoxyacetals to esters

Thomas J. Fisher, Patrick H. Dussault

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Hypochlorites efficiently dehydrate hydroperoxyacetals to furnish the corresponding esters. The reaction, which can be accomplished with stoichometric Ca(OCl)2 or with catalytic amounts of t-BuOCl, appears to involve formation and heterolytic fragmentation of secondary chloroperoxides, species not previously described in solution chemistry.

Original languageEnglish (US)
Pages (from-to)5615-5617
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number42
DOIs
StatePublished - Oct 20 2010

Fingerprint

Hypochlorous Acid
Dehydration
Esters

Keywords

  • Chloroperoxide
  • Ester
  • Fragmentation
  • Hydroperoxyacetal
  • Hypochlorite

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Fragmentation of chloroperoxides : Hypochlorite-mediated dehydration of hydroperoxyacetals to esters. / Fisher, Thomas J.; Dussault, Patrick H.

In: Tetrahedron Letters, Vol. 51, No. 42, 20.10.2010, p. 5615-5617.

Research output: Contribution to journalArticle

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KW - Chloroperoxide

KW - Ester

KW - Fragmentation

KW - Hydroperoxyacetal

KW - Hypochlorite

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