New spiro derivatives of penicillin |
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Authors: | Lam Chan Stephen A Matlin |
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Institution: | Chemistry Department, The City University, Northampton Square, London ECIV OHB UK |
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Abstract: | The first example of carbenoid ring expansion of thiophene to a 2H-thiopyran has been observed in its Rh-catalysed reaction with benzhydryl 6-diazopenicillanate. Buchner ring expansion of anisole with the same carbenoid gives two isomeric methoxy-cycloheptatrienes by attack on the upper face of the β-lactam ring. In one of the isomers, the methoxyl group shows a strong conformational preference in solution, revealed by n.O.e. difference speotroscopy. |
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