Ammonia-promoted fragmentation of 2-alkyl- and 2,4-dialkyl-3-iodo-1- oxocyclohexan-2,4-carbolactones |
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Authors: | Dai Mingshi Zhang Xuqing Khim Seock-Kyu Schultz Arthur G |
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Affiliation: | Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York 12180, USA. |
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Abstract: | 2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo ammonia-promoted fragmentation reactions to provide butenolides, gamma-butyrolactone, and/or beta,gamma-epoxycyclohexanones. Product distribution is governed by the relative size of the substituents at C-2 and C-4 of the cyclohexanones. Butenolide amide, the major product from the fragmentation, is further converted into their respective piperidinone and pyrrolidine derivatives. |
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