135922-84-8Relevant articles and documents
PROSTANOIDS. XLIV. FUNCTIONALIZATION OF 6-OXO-7,7-DICHLOROBICYCLOHEPT-2-ENE ACCORDING TO PRINS REACTION AS A KEY STAGE OF A RATIONAL APPROACH THE SYNTHONES FOR CARBOCYCLINES
Tolstikov, G. A.,Miftakhov, M. S.,Akhmetvaleev, R. T.,Zhurba, V. M.,Chertanova, L. N.,Khalilov, L. M.
, p. 1663 - 1669 (2007/10/02)
The Prins reaction of 6-oxo-7,7-dichlorobicyclohept-2-ene in a medium of glacial AcOH-H2SO4 (10:1) at 117 deg C proceeds with the formation of two main products: 7,7-dichloro-2β-acetoxymethyl-3α-acetoxybicycloheptan-6-one and 7,9-carbolactone-7-chloro-3-oxatricyclo6,8>nonane in a 2:1 ratio.In addition, two by-products (10percent) were isolated, the structures of which are related to the above compounds.The structure of one of the anomalous Prins adducts was more precisely defined by means of x-ray diffraction analysis, and the possible paths of their formation are discussed.The reaction of diacetate (the main Prins reaction product) with diazomethane proceeds nonselectively.At the same time, it monochloro derivative gives in a good yield the corresponding bicyclooctanone, which was converted by reductive dechlorination into desited 2β-acetoxymethyl-3α-acetoxybicyclooctan-7-one.
