Record Details
The preparation of 2-methoxy-4,5-dimethylstilbene and its photochemistry
ScholarsArchive at Oregon State University
| Field | Value |
|---|---|
| Title | The preparation of 2-methoxy-4,5-dimethylstilbene and its photochemistry |
| Names |
Tong, Homer Hin-Chau
(creator) Marvell, Elliot N. (advisor) |
| Date Issued | 1965-05-26 (iso8601) |
| Note | Graduation date: 1968 |
| Abstract | 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. |
| Genre | Thesis/Dissertation |
| Topic | Stilbene |
| Identifier | http://hdl.handle.net/1957/47085 |
