ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A simple synthesis of tetrachlorophenanthrene starting from DDT has been realized. 1,1,1,2-tetrachloro-2,2-bis-(4-chlorophenyl)-ethane (I) and its rearranged product 1,1,2,2-tetrachloro-1,2-bis-(4-chlorophenyl)-ethane (V) and other analogs substituted by halogen in the para-position undergo a cycliarylation yielding 3,6,9,10-tetrahalogenophenanthrenes. Partial dechlorination of this tetrachlorophenanthrene yields 3,6-dichlorophenanthrene. Oxidation gives 3,6-dichloro-9,10-phenanthrenequinone, and chlorosulfonation leads to 3,6,9,10-tetrachloro-2,7-bis-(chlorosulfonyl)-phenanthrene. The mechanism of this cyclization reaction in presence of LEWIS acids is discussed and compared with the cyclization of DDT derivatives to yield fluorenones.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19680510710
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