Prev. Article Next Article Table of Contents

Letter

O-TBS-N-tosylhydroxylamine: A Reagent for Facile Conversion of Alcohols to Oximes

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Katsushi Kitahara, Tatsuya Toma, Jun Shimokawa and Tohru Fukuyama

Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Org. Lett., 2008, 10 (11), pp 2259–2261

DOI: 10.1021/ol800677p

Publication Date (Web): April 30, 2008

Abstract

A variety of oximes were synthesized from the corresponding alcohols, alkyl halides, or alkyl sulfonates without using external oxidants. With this simple two-step procedure involving substitution with readily available TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared including the ones hardly preparable with conventional procedures.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Citing Articles

View all 4 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 3 ACS Journal articles (3 most recent appear below).

Total Synthesis of (+)-Epilupinine via An Intramolecular Nitrile Oxide-Alkene Cycloaddition
Deyong Su, Xinyan Wang, Changwei Shao, Jimin Xu, Rui Zhu, and Yuefei Hu
The Journal of Organic Chemistry2011 76 (1), 188-194
- Total Synthesis of (+)-Epilupinine via An Intramolecular Nitrile Oxide-Alkene Cycloaddition
  Deyong Su, Xinyan Wang, Changwei Shao, Jimin Xu, Rui Zhu, and Yuefei Hu
  The Journal of Organic Chemistry2011 76 (1), 188-194
  Total synthesis of (+)-epilupinine was accomplished in nine steps and in 48% overall yield, in which INOC was used as the key step for the construction of the quinolizidine skeleton. We found that it was an extremely difficult task to prepare the key ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Au/Ag-Cocatalyzed Aldoximes to Amides Rearrangement under Solvent- and Acid-Free Conditions
Rubén S. Ramón, Johann Bosson, Silvia Díez-González, Nicolas Marion and Steven P. Nolan
The Journal of Organic Chemistry2010 75 (4), 1197-1202
- Au/Ag-Cocatalyzed Aldoximes to Amides Rearrangement under Solvent- and Acid-Free Conditions
  Rubén S. Ramón, Johann Bosson, Silvia Díez-González, Nicolas Marion and Steven P. Nolan
  The Journal of Organic Chemistry2010 75 (4), 1197-1202
  The gold/silver-cocatalyzed conversion of aldoximes into primary amides is reported. The reaction, which proceeds under neat and acid-free conditions, allows for the conversion of a range of aldoximes, and is a rare example of cooperative catalysis ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
A Simple Synthesis of Nitriles from Aldoximes
Manish K. Singh and Mahesh K. Lakshman
The Journal of Organic Chemistry2009 74 (8), 3079-3084
- A Simple Synthesis of Nitriles from Aldoximes(1)
  Manish K. Singh and Mahesh K. Lakshman
  The Journal of Organic Chemistry2009 74 (8), 3079-3084
  Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH2Cl2, THF, or DMF. As an ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links