Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions

Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions
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DOI:
10.1070/mc2005v015n01abeh001946
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发表时间:
2005-01-01
影响因子:
1.9
通讯作者:
Litvinov, IA
Litvinov, IA
中科院分区:
化学4区
文献类型:
--
作者:
Militsina, OI;Kovyljaeva, GI;Litvinov, IA

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Heating the 16-E-oxime of isosteviol (ent-16-E-hydroxyiminobeyeran-19-oic acid) with concentrated hydrochloric acid (or 25% H2SO4) at 110 degreesC leads to the formation of lactone of 4alpha-carboxy-13alpha-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid as the main product, whereas approximately equal quantities of this lactone and lactam of 4alpha-carboxy- 13alpha-amino- 13,16- seco-ent-19 norbeyeran-16-oic acid are formed by heating the 16-E-oxime of isosteviol with concentrated hydrochloric acid in an ampoule at 180 degreesC.