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Benzo[a]heptalenes from Heptaleno[1,2-c]furans. Part 2 : Formation of Benzo[a]heptalenes with Methoxy Groups at the Benzo Part

✍ Scribed by Peter Uebelhart; Christophe Weymuth; Anthony Linden; Hans-Jürgen Hansen

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
720 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

Scheme 7 a) Ac 2 O/H 2 SO 4 , r.t. b) 1. TfOSiMe 3 /Et 3 N/CH 2 Cl 2 , r.t. 2. NH 4 Cl/H 2 O. a ) A 1 : 1 mixture 17a/18a (80%) was obtained and subjected to subsequent reactions without further purification. b ) After recrystallization 22%. c ) After crystallization 57%; 12% of 17b were recovered. d ) The not further purified mixture of (P*)-and (M*)-17b (77%) was subjected to subsequent reactions. e ) Brownish oil, which subsequently crystallized from a CDCl 3 solution. a ) Solvent hexane; data of 42 are taken from [28]. b ) Relative mdeg with respect to the most intense band (¼ 1.00) of the ( P)-configured benzo[a]heptalenes. c ) Unstructured tailing (neg. in CD ) up to 450 nm; see Fig. 3 in [28]. d ) No separation of the antipodes of 42 on an anal. Chiralcel-OD-H column in hexane at r.t.

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