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Unexpected migration of a benzoyl group in the intramolecular Wittig reaction of o-acyloxybenzylidenephosphoranes with benzoyl chlorides: one-pot synthesis of isomeric 3-benzoyl-2-phenylbenzofurans
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2020-01-20 , DOI: 10.1016/j.tetlet.2020.151634
Michela Begala , Michele Mancinelli , Giovanna Lucia Delogu

The reaction of o-acyloxybenzylidenetriphenylphosphoranes with substituted benzoyl chlorides in an aprotic solvent led, together with the expected 2-phenylbenzofuran, to isomeric 3-benzoyl-2-phenylbenzofuran derivatives. This result formally corresponds to intramolecular migration of the benzoyl group from the ortho oxygen atom to the ylide carbanion via cyclization and ring opening of the starting o-acyloxybenzylidenetriphenylphosphoranes.



中文翻译:

酰氧基亚苄基膦酸酯与苯甲酰氯的分子内Wittig反应中苯甲酰基的意外迁移:异构体3-苯甲酰基-2-苯基苯并呋喃的一锅合成

在非质子溶剂中,邻-酰氧基苄基亚氨基三苯基苯基膦与取代的苯甲酰氯的反应与预期的2-苯基苯并呋喃一起导致异构体3-苯甲酰基-2-苯基苯并呋喃衍生物。该结果形式上对应于苯甲酰基从氧原子通过环化和起始的邻-酰氧基苄基亚氨基三苯基磷ora烷的开环从分子内迁移至内酰碳负离子。

更新日期:2020-01-21
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