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.
1.pdf - Published Version
Restricted to Registered users only
Download (424Kb) | Request a copy
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|
|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|
Actions (login required)