Thioaldehyde Diels-Alder Reactions

E. Vedejs, T. H. Eberlein, D. J. Mazur, C. K. McClure, D. A. Perry, R. Ruggeri, E. Schwartz, J. S. Stults, D. L. Varie, R. G. Wilde, S. Wittenberger

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Abstract

Thioaldehydes containing virtually any a-substitutent can be generated by photofragmentation of phenacyl sulfides. Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advanced C-C bonding in the transition state. Acceptor-substituted thioaldehydes react in the opposite regiochemical sense with C-S bonding advanced. A number of unusual thioaldehydes have been trapped, including the parent HCH=S, Me3SiCHS, Ph2P(O)CH=S, PhSO2CH=S, and CNCH=S, as well as more conventional alkyl- or acyl-substituted derivatives.

Original languageEnglish (US)
Pages (from-to)1556-1562
Number of pages7
JournalJournal of Organic Chemistry
Volume51
Issue number9
DOIs
StatePublished - Jan 1 1986

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Vedejs, E., Eberlein, T. H., Mazur, D. J., McClure, C. K., Perry, D. A., Ruggeri, R., Schwartz, E., Stults, J. S., Varie, D. L., Wilde, R. G., & Wittenberger, S. (1986). Thioaldehyde Diels-Alder Reactions. Journal of Organic Chemistry, 51(9), 1556-1562. https://doi.org/10.1021/jo00359a034