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Allylic Reactions of Benzocyclopropenes. Discrimination of halogen substituents in 1, 1‐Dihalogenobenzocyclopropenes
Author(s) -
Müller Paul,
Etienne Robert,
Pfyffer Jean,
Pineda Nelson,
Schipoff Michel
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610719
Subject(s) - chemistry , aromatization , halogen , allylic rearrangement , fluoride , base (topology) , medicinal chemistry , organic chemistry , catalysis , inorganic chemistry , mathematical analysis , alkyl , mathematics
Reaction of 1, 1‐dichloro‐2, 5‐diphenylbenzocyclopropene ( 10a ) with 1 equiv. of silver fluoride yields 1‐chloro‐1‐fluoro‐2, 5‐diphenylbenzocyclopropene ( 10c ). Both 10a and 10c react with excess silver fluoride to give the difluoro compound 10b . Both 10b and 10c are also prepared via cyclo‐additions of 1, 2‐dichloro‐3, 3‐difluorocyclopropene ( 14 ) or 1, 2, 3‐flurocyclopropene ( 13 ) with diphenylbutadiene and subsequent aromatization with base. Similarly. 1‐chloro‐1‐fluorobenzocyclopropene ( 16 ) is accessible from butadiene and 13 .