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ChemInform Abstract: Formation of Heptaleno(1,2-c)furans and Heptaleno(1,2-c)furanones.

✍ Scribed by P. UEBELHART; P. MOHLER; R.-A. FALLAHPOUR; H.-J. HANSEN


Book ID
112024074
Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
26
Category
Article
ISSN
0931-7597

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Benzo[a]heptalenes from Heptaleno[1,2-c]
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## Abstract It is shown that heptaleno[1,2‐__c__]furans 1, which are available in two steps from heptalene‐4,5‐dicarboxylates by reduction and oxidative dehydrogenation of the corresponding vicinal dimethanols 2 with MnO~2~ or IBX (__Scheme 4__), react thermally in a __Diels–Alder__‐type [4+2] cycl

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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.

Formation of 6-Methyl-7,11-diphenylhepta
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## Abstract The dehydrogenation reaction of a mixture of heptalene‐1,2‐ and heptalene‐4,5‐dimethanols **4a** and **4b** with basic MnO~2~ in AcOEt at room temperature led to the formation of the corresponding heptaleno[1,2‐__c__]furan‐1‐one **6a** and heptaleno[1,2‐__c__]furan‐3‐one **7a** (__Schem