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Vicarious nucleophilic substitution of hydrogen in nitro-1,6-methano[10]annulenes

✍ Scribed by S. Ostrowski; R. J. Moritz; B. Mudryk


Publisher
Springer Vienna
Year
1995
Tongue
English
Weight
849 KB
Volume
126
Category
Article
ISSN
0026-9247

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Vicarious Nucleophilic Substitution (VNS
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## Abstract Azulene reacts with carbanions bearing a leaving group according to the vicarious nucleophilic substitution (VNS) scheme. Treatment of 6‐chloroazulene with such carbanions affords the VNS reaction and nucleophilic aromatic substitution (S~N~Ar) products. magnified image

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Dedicated to Professor Mirhoel Hunack on the occasion of his 65th birthday (1 6.VII. 96) The treatment of bromo-substituted 1,6-methano[lO]annulenes with sodium thiolates in DMF provides easy access to alkylthio-and arylthio-substituted 1,6-methano[l0]annulenes (Schemes 2 4 ) . These compounds are