Studies on the conversions of diols and cyclic ethers-491 1 Part 48 in this series

Á. Molnár and M. Bartók, Helv. Chim. Acta submitted for publication. Stereochemistry of cyclodehydration of 1,4-diols on the action of brönsted and lewis acids: a comprehensive study

Árpád Molnár, K. Felföldi, M. Bartók

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44 Citations (Scopus)

Abstract

The stereochemistry of the cyclodehydration of (±)- and meso-2,5-hexanediol on the action of various dehydrating agents was investigated. The earlier assumed and confirmed intramolecular SN2 mechanism for acid-catalysed ring-closure was found to hold in most cases. Various extents of racemisation can be observed on the action of certain Lewis acids, and the solvents concentrated H2SO4 and HMPT (hexamethyl phosporic acid triamide) under previously unexamined reaction conditions.

Original languageEnglish
Pages (from-to)2149-2151
Number of pages3
JournalTetrahedron
Volume37
Issue number11
DOIs
Publication statusPublished - 1981

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Cyclic Ethers
Lewis Acids
Stereochemistry
Publications
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Studies on the conversions of diols and cyclic ethers-491 1 Part 48 in this series: {\'A}. Moln{\'a}r and M. Bart{\'o}k, Helv. Chim. Acta submitted for publication. Stereochemistry of cyclodehydration of 1,4-diols on the action of br{\"o}nsted and lewis acids: a comprehensive study",
abstract = "The stereochemistry of the cyclodehydration of (±)- and meso-2,5-hexanediol on the action of various dehydrating agents was investigated. The earlier assumed and confirmed intramolecular SN2 mechanism for acid-catalysed ring-closure was found to hold in most cases. Various extents of racemisation can be observed on the action of certain Lewis acids, and the solvents concentrated H2SO4 and HMPT (hexamethyl phosporic acid triamide) under previously unexamined reaction conditions.",
author = "{\'A}rp{\'a}d Moln{\'a}r and K. Felf{\"o}ldi and M. Bart{\'o}k",
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T1 - Studies on the conversions of diols and cyclic ethers-491 1 Part 48 in this series

T2 - Á. Molnár and M. Bartók, Helv. Chim. Acta submitted for publication. Stereochemistry of cyclodehydration of 1,4-diols on the action of brönsted and lewis acids: a comprehensive study

AU - Molnár, Árpád

AU - Felföldi, K.

AU - Bartók, M.

PY - 1981

Y1 - 1981

N2 - The stereochemistry of the cyclodehydration of (±)- and meso-2,5-hexanediol on the action of various dehydrating agents was investigated. The earlier assumed and confirmed intramolecular SN2 mechanism for acid-catalysed ring-closure was found to hold in most cases. Various extents of racemisation can be observed on the action of certain Lewis acids, and the solvents concentrated H2SO4 and HMPT (hexamethyl phosporic acid triamide) under previously unexamined reaction conditions.

AB - The stereochemistry of the cyclodehydration of (±)- and meso-2,5-hexanediol on the action of various dehydrating agents was investigated. The earlier assumed and confirmed intramolecular SN2 mechanism for acid-catalysed ring-closure was found to hold in most cases. Various extents of racemisation can be observed on the action of certain Lewis acids, and the solvents concentrated H2SO4 and HMPT (hexamethyl phosporic acid triamide) under previously unexamined reaction conditions.

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JO - Tetrahedron

JF - Tetrahedron

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