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Reactions of 3,5‐Diaryl‐1,2‐dithiolium Salts and 3,5‐Diaryl‐1,2,4‐dithiazolium Salts with Metal Cyclopentadienides
Author(s) -
Hartke Klaus,
Kraska Andreas,
Massa Werner,
Molinier Michel,
Wocadlo Sigrid
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970133
Subject(s) - chemistry , boron trifluoride , lewis acids and bases , intramolecular force , catalysis , metal , ether , medicinal chemistry , tricyclic , ring (chemistry) , condensation , polymer chemistry , boron , organic chemistry , physics , thermodynamics
Reaction of the 3,5‐diaryl‐1,2‐dithiolium salts 2 with the metal cyclopentadienides 4 and 9 leads to the formation of the tricyclic compounds 6 and 10 via a ring‐opened intermediate, which undergoes an intramolecular Diels‐Alder cyclization. Compounds 6 and 10 rearrange by treatment with boron trifluoride‐diethyl ether to the isomeric compounds 7 and 11 . The structures 6f and 7f were confirmed by X‐ray analysis. Condensation of the 3,5‐diaryl‐1,2,4‐dithiazolium salts 3 with the metal cyclopentadienides 4 affords the tricyclic compounds 12 , which do not rearrange by Lewis acid catalysis.