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The use of tosylhydrazone salts as a safe alternative for handling diazo compounds and their applications in organic synthesis

journal contribution
posted on 2023-06-07, 21:43 authored by J Robin Fulton, Varinder K Aggarwal, de Vicente Javier
Diazo compounds are useful synthetic intermediates in organic synthesis but, due to their toxicity and unpredictable explosive behaviour, their unique reactivity has not been fully exploited and their use on large scale has been avoided. We have developed a reliable method that generates diazo compounds in situ. Our approach is based on the Bamford-Stevens reaction, which utilizes tosylhydrazone salts as diazo precursors. In the presence of phase-transfer-catalysts (PTC), we found that tosylhydrazone salts can be cleanly converted to diazo compounds under mild reaction conditions and in a wide range of solvents. These diazo compounds can then be induced to react directly with alkenes or alkynes to synthesize pyrazoles or with aldehydes to generate ketones. Alternatively, diazo compounds can react with transition metals capable of carbene transfer reactions. We have shown the usefulness of this chemistry in a number of different transformations, such as Wittig olefination reactions and the sulfur ylide mediated epoxidation, as well as aziridination and cyclopropanation chemistry as applied toward the synthesis of more complicated molecules. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

History

Publication status

  • Published

Journal

European Journal of Organic Chemistry

ISSN

1434-193X

Issue

8

Volume

-

Page range

1479-1492

Pages

13.0

Department affiliated with

  • Chemistry Publications

Notes

Invited review. JRF compiled a summary of results from the VKA group detailing his unique method for safely handling diazo compounds. JRF was main contributor, VKA and JV edited.

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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