210684-62-1Relevant 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.
TEMPO free radical derived β-aminoalkoxyketolactones: Substrates for base-, acid- and radical-induced fragmentation reactions
Schultz, Arthur G.,Zhang, Xuqing
, p. 399 - 400 (2007/10/03)
β-Aminoalkoxyketolactones 2 and 3 obtained from the TEMPO free radical substitution of iodolactones 1 undergo fragmentations under basic, acidic and free radical conditions.
