The preparation of 2-methoxy-4,5-dimethylstilbene and its photochemistry Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/5q47rr45p

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  • During a study of the abnormal dienone-phenol rearrangement discovered by Marvell and Geiszler, Imel (1960) found that 4-oxo-3,3-dimethyl-3,4-dihydrophenanthrene rearranged slowly to a phenol which was tentatively identified as 3,4-dimethyl-l-phenanthrol; further evidence to support this assignment was deemed essential. The recent work by Mallory on the photochemical conversion of stilbenes to phenanthrenes suggested a convenient synthesis of 3,4-dimethyl-l-phenanthrol by demethylating the expected product, 1-methoxy-3,4-dimethylphenanthrene, obtained from the ultraviolet irradiation of 2-methoxy-4,5-dimethylstilbene. This substituted stilbene was synthesized by unequivocal methods and the structure confirmed by spectral methods. Irradiation of the stilbene yielded a different and unexpected product which was identified as 2,3-dimethylphenanthrene (10%), in addition to seven other products. The factors which determine the course of the ring closure step in unsymmetrical cases like that investigated here are not yet clear.
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  • File scanned at 300 ppi using Capture Perfect 3.0 on a Canon DR-9050C in PDF format. CVista PdfCompressor 5.0 was used for pdf compression and textual OCR.
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  • description.provenance : Approved for entry into archive by Katy Davis(kdscannerosu@gmail.com) on 2014-04-07T17:34:15Z (GMT) No. of bitstreams: 1 TongHomerHC1968_Redacted.pdf: 917630 bytes, checksum: ee011a01d5c221ed44841d104f495313 (MD5)
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