Reddy, Parameswara M and Rao, Krishna GS (1981) Applications of the Vilsmeier reaction. 13. Vilsmeier approach to polycyclic aromatic hydrocarbons. In: Journal of Organic Chemistry, 46 (26). pp. 5371-5373.
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Abstract
The Synthesis of three typical polycyclic hydrocarbons (PAH) has been described, wherein the Vilsmeier reaction plays a major role. Vilsmeier reaction of the tetraloll gives the dihydronaphthaldehyde 2 which on cyclodehydration gives the dihydroarene 3. Ita dehydrogenation affords 3-methoxybenz[a]anthracene (4). Vilsmeier reaction on the dimethoxydihydronaphthalene 5 gives the versatile dimethoxydihydronaphthaldehyde 6 which has been converted to the dimethoxybenzo[c]fluorene 7 by direct cyclodehydration and the fulvene 10 by cyclodehydration of allylic alcohol 8 derived from 6 followed by dehydrogenation. The saturated alcohol 12 corresponding to 8 undergoes cyclodehydration to give the dimethoxyhexahydrobenzo[c]phenanthrene (13). Some of the advantages of the Vilsmeier approach to PAH have been pointed out.
Item Type: | Journal Article |
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Publication: | Journal of Organic Chemistry |
Publisher: | American Chemical Society |
Additional Information: | Copy right of this article belongs to American Chemical Society. |
Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
Date Deposited: | 28 Aug 2009 08:51 |
Last Modified: | 03 Aug 2011 10:48 |
URI: | http://eprints.iisc.ac.in/id/eprint/22609 |
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