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Sulfonyl nitrene

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Generic chemical structure of a sulfonyl nitrene

A sulfonyl nitrene is a chemical compound with generic formula RSO2N. Known sulfonyl nitrenes include methyl sulfonyl nitrene, trifluoromethyl sulfonyl nitrene, and tolyl sulfonyl nitrene. Also fluorosulfonyl nitrene FSO2N exists, but rearranges to FNSO2. Preparation of sulfonyl nitrenes can be accomplished by heating sulfonyl azides:

RSO2N3 → RSO2N + N2

They are distinct from sulfinyl nitrenes which only have one oxygen attached to the sulfur atom.

References

  1. Shainyan, Bagrat A.; Kuzmin, Anton V. (February 2014). "Sulfonyl nitrenes from different sources: computational study of formation and transformations". Journal of Physical Organic Chemistry. 27 (2): 156–162. doi:10.1002/poc.3254.
  2. Zeng, Xiaoqing; Beckers, Helmut; Willner, Helge (4 February 2013). "Thermally Persistent Fluorosulfonyl Nitrene and Unexpected Formation of the Fluorosulfonyl Radical". Journal of the American Chemical Society. 135 (6): 2096–2099. Bibcode:2013JAChS.135.2096Z. doi:10.1021/ja312073w. PMID 23363420.
  3. Abramovitch, Rudolph A.; Knaus, G. N.; Uma, V. (December 1969). "Aromatic substitution by sulfonyl nitrenes. Singlet or triplet reactive intermediates". Journal of the American Chemical Society. 91 (26): 7532–7533. Bibcode:1969JAChS..91.7532A. doi:10.1021/ja01054a065.


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