Oxidation of Arylthiourea by Cetyltrimethylammonium Dichromate

Abstract

With a view to investigate the oxidation behaviors of cetyltrimethylammonium dichromate on multifunctional groups, some arylthioureas were subjected to oxidation, both in neutral and in acidic conditions. In neutral conditions, the products were found to be a mixture of corresponding urea and isonitrile. In acidic conditions, the products were corresponding ureas only. A probable mechanism was proposed for the formation of the product, wherein the first step involves coupling of –NH₂ and –SH of one molecule to the –NH₂ and –SH of another molecule, respectively, which is followed by removal of nitrogen and sulfur. The microwave irradiation resulted in great yield of isonitrile than urea in neutral conditions.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

Keywords:

• Cetyltrimethylammonium dichromate
• isonitrile
• thiourea

ACKNOWLEDGMENTS

B. K. M. thanks the University Grants Commission, New Delhi, for financial assistance through a research project. S. S. thanks the Council of Scientific and Industrial Research, New Delhi, for a senior research fellowship.

Notes

Note. The yields are on isolation basis.