17. Preparation and Uses of Isotopically Labeled Derivatives

  1. Zvi Rappoport
  1. Barry K. Carpenter

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch17

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Carpenter, B. K. (1987) Preparation and Uses of Isotopically Labeled Derivatives, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch17

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, Cornell University, Ithaca, New York 14853-1301, USA

Publication History

  1. Published Online: 28 JAN 2005
  2. Published Print: 28 OCT 1987

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai

ISBN Information

Print ISBN: 9780471917380

Online ISBN: 9780470023440

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Summary

This chapter contains sections titled:

  • Introduction

  • Synthetic Methods

    • Carbene or Carbenoid Addition to Stereospecifically Deuterated Alkenes

    • The Haller–Bauer Reaction

    • Catalytic Decarbonylation of Aldehydes

    • Reduction of Halocyclopropanes

    • Cyclopropane Ring-closure by Stereoselective Nucleophilic Displacement

    • Nucleophilic Addition to Cyclopropenes

  • Thermal Rearrangements

    • Stereomutation of Cyclopropanes

      • Formulation of the Problem

      • Stereomutation of Trans-1,2-dimethyl-1,2-bis(trideuteriomethyl)cyclopropane

      • Stereomutation of Optically Active trans-cyclopropane-1,2-d2

      • Stereomutation of Labeled Phenylcyclopropanes

      • Stereomutation of Vinylcyclopropane-2,3-d2

      • Stereomutation of 2-phenylcyclopropane-1,3-d2-1-carbonitrile

      • Stereomutation of Spiro[2.2]pentane-2,3-d2

      • Stereomutation of 1-methylspiro[2.4]hepta-4,6-diene-d

    • The Cyclopropane–Propene and Related Rearrangements

    • The Vinylcyclopropane Rearrangement

      • Formulation of the Problem

      • Vinylcyclopropane-2-d and -2,3-d2

      • (R,R)-trans-2-Methyl-1-(3,3-dimethyl-1-buten-1,1-d2-2-yl)cyclopropane

      • Bicyclo[3.1.0]hexene and Related Compounds

      • Bicyclo[2.1.1]hexene-5-d and Related Compounds

    • Thermal Reactions of Labeled Cyclopropenes

      • Methanolysis of Tetrachlorocyclopropene

      • Cyclopropene as an Intermediate in the Propyne–allene Interconversion

      • Allylic Rearrangement in the Decarbonylation of (2-cyclopropene-1-carbonyl)rhenium Compounds

    • The Methylenecyclopropane Rearrangement

      • Formulation of the Problem

      • Deuterium Kinetic Isotope Effects on the Thermal Rearrangement of Methylenecyclopropanes

      • Formation and Rearrangement of 2-methoxy-5-(Methylene-d)bicyclo[2.1.0] Pentane

      • Pyrolysis of 1-(Methylene-d2)-2-(Vinyl-d3) Cyclopropane

      • Reaction of 2-phenyl-, 2,2-diphenyl- and trans-2,3-diphenylmethylene Cyclopropanes-3-d with Iron Carbonyl Reagents

    • Rearrangements of Labeled Bicyclo[6.1.0]nona-2,4,6-trienes

      • Thermal Unimolecular Rearrangement

    • Deuterium Isotope Effects on Pyrazoline Decomposition

  • Cation Reactions

    • Protonated Cyclopropanes

    • The Cyclopropylcarbinyl Cation

  • Anion Reactions

    • Cyclopropyl Anions

    • Triphenylcyclopropenyl Anion

  • Radical and Carbene Reactions

    • Cyclopropyl Radicals

    • Cyclopropenylmethylene, Bicyclobutanylidene and Tetrahedrane

  • Photochemistry

    • Degenerate Rearrangement of Benzvalene

    • Photochemistry of Bicyclo[1.1.0]butane

  • References