Ammonia-promoted fragmentation of 2-alkyl- and 2,4-dialkyl-3-iodo-1- oxocyclohexan-2,4-carbolactones.
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.
Dai
Mingshi
M
Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.
Zhang
Xuqing
X
Khim
Seock-Kyu
SK
Schultz
Arthur G
AG
D000641:Ammonia / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure
D003512:Cyclohexanones; D007202:Indicators and Reagents; D007783:Lactones; D000641:Ammonia; D008094:Lithium