95931-34-3Relevant articles and documents
Reaction of 2'-Hydroxychalcones with Methylene Iodide: A Novel Formation of 3-Aryl-2,5-dihydro-5-oxo-1-benzoxepins
Jain, A. C.,Nayyar, Naresh K.,Sharma, B. N.
, p. 1211 - 1215 (2007/10/02)
2'-Hydroxychalcones (1a-c) bearing a methoxy group at 4'-position react with methylene iodide in the presence of K2CO3 and Me2CO for 38 hr to give besides the corresponding flavanones (2a-c), 3-aryl-2,5-dihydro-5-oxo-1-benzoxepins (3a-c).However, the 2'-hydroxychalcones (1d and 1e), having 4',6'-dimethoxy groups react sluggishly requiring 170 hr and also the product is a mixture of not only the corresponding flavanones (2d,e) and benzoxepinones (3d,e) as above but also of the biscompounds (4a,b) having intermolecular methylenedioxy group.The structures of benzoxepinones (3) have been established by their PMR, 13C-NMR and mass spectral data.Their formation has been rationalised via the formation of cyclopropane ring (5), followed by ring cleavage and H- shift.