Naphthyl‐Substituted Carbocations: From  peri  Interaction to Cyclization | Zendy

Dyker Gerald | Zendy; Hagel Marcel | Zendy; Henkel Gerald | Zendy; Köckerling Martin | Zendy

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Naphthyl‐Substituted Carbocations: From peri Interaction to Cyclization

Author(s) -

Dyker Gerald,

Hagel Marcel,

Henkel Gerald,

Köckerling Martin

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800124

Subject(s) - chemistry , carbocation , cleavage (geology) , ring (chemistry) , furan , nuclear magnetic resonance spectroscopy , stereochemistry , regioselectivity , medicinal chemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering , catalysis

The peri interaction of 1‐functionalized naphthalenes equipped with a triarylmethyl cation at the 8‐position has been studied because of the reversibility of the ring‐closing reaction, which was monitored closely by NMR spectroscopy in the case of the cyclic ammonium salt 5b . Carbocycle 4a and N‐heterocycle 5b did not exhibit any tendency for ring cleavage under various conditions, whereas the naphtho‐annulated furan 4c underwent reversible ring cleavage under strongly acidic conditions.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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