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Ring Expansions of Oxiranes and Oxetanes

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Synthesis of 4- to 7-membered Heterocycles by Ring Expansion

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 41))

Abstract

This chapter is focused on recently published (2006–2014) oxirane and oxetane ring-expansion reactions. The majority of these advances employ oxirane substrates, the discussion of which is broken into five thematic sections representing insertions, cascades, metal-free, metal-catalyzed, and miscellaneous strategies. Oxetane ring-expansion reactions are still rare and are discussed together in one section. A concise graphical summary has been created for every new contribution to this area, highlighting reagents, reaction conditions, scope, mechanistic proposals, and asymmetry where applicable. This review chapter should enable researchers new to the field to quickly assess the current state of the art.

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Abbreviations

AgOTf:

Silver triflate

CO:

Carbon monoxide

CSA:

Camphorsulfonic acid

DCE:

1,2-Dichloroethane

DCM:

Dichloromethane

DME:

Dimethoxyethane

DMF:

Dimethylformamide

EMIMBr:

1-Ethyl-3-methylimidazolium bromide

HBr:

Hydrobromic acid

HCl:

Hydrochloric acid

HEMIMB:

1-(2-hydroxyl-ethyl)-3-methylimidazolium bromide

hfacac:

Hexafluoroacetylacetonate

HFIP:

Hexafluoroisopropanol

HI:

Hydroiodic acid

In(OTf)3 :

Indium(III) triflate

LDA:

Lithium diisopropylamide

MsCl:

Methanesulfonyl chloride

MTBE:

Methyl tert-butyl ether

MTHF:

2-Methyltetrahydrofuran

NBS:

N-Bromosuccinimide

NCS:

N-Chlorosuccinimide

NIS:

N-Iodosuccinimide

PET:

Photosensitized electron transfer

PMA:

Phosphomolybdic acid

PTA:

Phosphotungstic acid

TESOTf:

Triethylsilyl triflate

TFA:

Trifluoroacetic acid

TfOH:

Triflic acid

TMSCN:

Trimethylsilyl cyanide

TPTP:

2,4,6-Triphenylthiapyrylium perchlorate

TsOH:

p-Toluenesulfonic acid

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Author information

Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ, 85721, USA

    David T. Smith & Jon T. Njardarson

Authors
  1. David T. Smith
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  2. Jon T. Njardarson
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Corresponding author

Correspondence to Jon T. Njardarson .

Editor information

Editors and Affiliations

  1. Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering Ghent University, Ghent, Belgium

    Matthias D’hooghe

  2. Department of Chemistry, Hankuk University of Foreign Studies, Yongin-si, Korea (Republic of)

    Hyun-Joon Ha

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Smith, D.T., Njardarson, J.T. (2015). Ring Expansions of Oxiranes and Oxetanes. In: D’hooghe, M., Ha, HJ. (eds) Synthesis of 4- to 7-membered Heterocycles by Ring Expansion. Topics in Heterocyclic Chemistry, vol 41. Springer, Cham. https://doi.org/10.1007/7081_2015_147

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