Concerted cycloaddition of chlorosulfonyl isocyanate to α-pinene stepwise rearrangement of the β-lactam cycloadduct to a γ-lactam |
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| Authors: | G.T. Furst M.A. Wachsman J. Pieroni J.G. White E.J. Moriconi |
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| Affiliation: | Department of Chemistry, Fordham University, New York, U.S.A. |
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| Abstract: | Chlorosulfonyl isocyanate adds to α-pinene in concerted fashion to give the unrearranged N-chlorosulfonyl-β-lactam 2 (75%). Thermolysis of cycloadduct 2 affords the rearranged N-chlorosulfonyl-γ-lactam 6 (60%) via a sequence of transient carbonium ions (45). Reductive hydrolysis of 2 and 6 gave, respectively, the NH-β-lactam 3 (70%) and the NH-γ-lactam 7 (70%). Proof of structure of the rearranged γ-lactams 6 and 7 are provided, respectively, by X-ray crystallographic analysis and the application of the Eu(dpm)3 NMR shift reagent. |
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| Keywords: | To whom correspondence should be addressed. Current address: Sandoz A. G. Farben/Chemikalien-Departement CH-4002 Basel Switzerland. |
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