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Synthesis 1999; 1999(2): 231-233
DOI: 10.1055/s-1999-3388
short paper
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Nitration of Benzoyl-Substituted Ketene Dithioacetals and Heterocyclic Aminals

Zhan-Jiang Li* , Qiang Yang, Xiao-Min Chen, Zhi-Tang Huang
  • *Institute of Chemistry, Academia Sinica, Beijing 100080, People's Republic of China; Fax +86(10)62 56 95 64; E-mail: huangzt@public.bta.net.cn
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Publication Date:
31 December 1999 (online)

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Nitration of benzoyl-substituted ketene dithioacetals 1 and heterocyclic ketene aminals 2-5 were investigated. The dithioacetals 1 underwent aromatic nitration and oxidation with nitric acid-sulfuric acid to give 6. Heterocyclic ketene aminals 2 and 3 underwent ethylenic nitration instead of aromatic nitration with nitric acid-acetic acid to afford 7 and 8 respectively, however, heterocyclic ketene aminals 4 and 5 failed to undergo nitration.

nitration - ketene dithioacetal - heterocyclic ketene aminal