Issue 35, 2013
From the journal:

RSC Advances

A simple and efficient method for mild and selective oxidation of propargylic alcohols using TEMPO and calcium hypochlorite†

Sabbasani Rajasekhara Reddyab  and  Anju Chadha*bc  

* Corresponding authors

a School of Advanced Sciences, Organic Chemistry Division, VIT University, VELLORE: 632014, Chennai 600036, India
E-mail: sekharareddyiitm@gmail.com

b Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600036, India
E-mail: anjuc@iitm.ac.in
Fax: +91 44 2257 4102
Tel: +91 44 2257 4106

c National Center for Catalysis Research, Indian Institute of Technology Madras, Chennai 600036, India

Abstract

Oxidation of propargylic alcohols to the corresponding aldehydes and ketones was achieved at room temperature using 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and calcium hypochlorite (Ca(OCl)2). Propargylic diols yielded corresponding dialdehydes as the product. This system was found to be very efficient for both the electron donating and electron withdrawing groups such as methoxy and nitro substituted alcohols, respectively. This method does not require any additives and demonstrates the controlled, selective oxidation of propargylic alcohols affording up to 97% isolated yield.

Graphical abstract: A simple and efficient method for mild and selective oxidation of propargylic alcohols using TEMPO and calcium hypochlorite

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Article information

DOI
https://doi.org/10.1039/C3RA41721B
Article type
Communication
Submitted
17 Apr 2013
Accepted
09 Jul 2013
First published
10 Jul 2013

RSC Adv., 2013,3, 14929-14933

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A simple and efficient method for mild and selective oxidation of propargylic alcohols using TEMPO and calcium hypochlorite

S. R. Reddy and A. Chadha, RSC Adv., 2013, 3, 14929 DOI: 10.1039/C3RA41721B

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