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Iodolactonization
・ Iodomethylzinc iodide
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Iodolactonization : ウィキペディア英語版
Iodolactonization
Iodolactonization (or, more generally, Halolactonization) is an organic reaction that forms a ring (the lactone) by the addition of an oxygen and iodine across a carbon-carbon double bond. The reaction was first reported by M. J. Bougalt in 1904 and has since become one of the most effective ways to synthesize lactones. Strengths of the reaction include the mild conditions and incorporation of the versatile iodine atom into the product.
:
Iodolactonization has been used in the synthesis of many natural products including those with medicinal applications such as vernoplepin and vernomenin, two compounds used in tumor growth inhibition, and vibralactone, a pancreatic lipase inhibitor that has been used in the treatment of obesity. Iodolactonization has also been used by E.J. Corey to synthesize numerous prostaglandins.
==History==
Bougalt's report of iodolactonization represented the first example of a reliable lactonization that could be used in many different systems. Bromolactonization was actually developed in the twenty years prior to Bougalt’s publication of iodolactonization.〔 However, bromolactonization is much less commonly used because the simple electrophilic addition of bromine to an olefin, seen below, can compete with the bromolactonization reaction and reduce the yield of the desired lactone.
Chlorolactonization methods first appeared in the 1950s〔 but are even less commonly employed than bromolactonization. The use of elemental chlorine is procedurally difficult because it is a gas at room temperature, and the electrophilic addition product can be rapidly produced as in bromolactonization.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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