796866-71-2Relevant academic research and scientific papers
Novel fragmentation reaction of 2-alkyl- and 2,4-dialkyl-3-iodo-1- oxocyclohexan-2,4-carbolactones
Khim, Seock-Kyu,Dai, Mingshi,Zhang, Xuqing,Chen, Lei,Pettus, Liping,Thakkar, Kshitij,Schultz, Arthur G.
, p. 7728 - 7733 (2007/10/03)
2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo lithium hydroxide- and lithium alkoxide-induced fragmentation reactions to provide butenolides, γ-hydroxycyclohexenones, and/or γ- butyrolactones. In general, product distribution is governed by two factors: (1) the nature of nucleophiles and (2) the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanones. Lithium hydroxide-induced fragmentation provides butenolides and γ-hydroxycyclohexenones. In contrast, lithium alkoxide-promoted fragmentation results in predominantly 5-substituted γ-butyrolactones along with a small amount of butenolides in limited cases. Fragmentation products induced by lithium hydroxide are largely influenced by the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanone ring. The bulky substituents render the exclusive formation of butenolides.
Asymmetric synthesis fragmentation reactions of 2-alkyl- and 2,4- dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones. Single enantiomer preparation of Δ(α,β)-butenolides, 2-alkyl-4-hydroxy-2-cyclohexen-1-ones and butyrolactones
Schultz, Arthur G.,Dai, Mingshi,Khim, Seock-Kyu,Pettus, Liping,Thakkar, Kshitij
, p. 4203 - 4206 (2007/10/03)
Fragmentation reactions of keto iodolactones 4 provide access to butenolides 5,2-alkyl-4-hydroxy-2-cyclohexen-1-ones 6, and butyrolactones 9. Δ(α,β)-Butenolides 5e and 5f were converted to heterocytes 14-16 by way of intramolecular cycloaddition reactions
