Fulvenes and Fulvalenes of a Heterocyclic System with 12π Electrons—Pseudophenafulvenes and Pentapseudophenafulvalenes

Die Reduktion von 2-Methyl-3H-naphtho [ 1,8-bc]thiophen-3-on (1 a) mit NaBH,/AlCl, oder NaBH,CN fuhrt zum Naphtholderivat 2. Mit den Ketenen 3a -c werden aus den Thia-pseudophenalenonen 1 a, b die Thia-pseudophenafulvene 5a -d erhalten, wobei 5d als Isomerengemisch 5d/I und Sd/II vorliegt. Aus l a wurde mit 1-Carbonyltetralin und mit 9-Carbonylfluoren das Fulven 6 bzw. das Thia-dibenzopentapseudophenafulvalen 7 erhalten. Aus 2-Brom-bzw. 2-Phenyl-5H-naphtho[l,8-bc]thiophen-5-on (8a,b) werden mit Diphenylketen und tert-Butylcyanketen die Thia-pseudophenafulvene 9a -c (9b,c als Isomerengemische) isoliert; aus Phenalenon und den asymmetrischen Ketenen 3 b sowie 3c werden die Isomerengemische 10a und b erhalten. Die

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Synthesen und chemische Eigenschaften neuer «Donor‐Akzeptor»‐stabilisierter Molekülsysteme mit zentraler Bicyclo [4.4.1]undeca‐l (10), 3,6,8‐tetraen‐2,5‐diyliden‐Gruppe

Neidlein

Zeiner

1982

Helvetica Chimica Acta

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Syntheses and Chemical Properties of New ‘Donor‐Acceptor’‐stahilized Molecular Systems with a Central Bicyclo[4.4.1] undeca‐l(10).3,6,8‐tetraene‐2,5‐diylidenc Group The synthesis of X‐methyl‐2‐(5‐oxobicyclo[4.4.1]undeca‐l)10(,3,6,8‐tetraen‐2‐yliden)‐l,3‐benzodithiol (4) is described starting with the keto‐enol mixture 2 and 5‐methyl‐1,3‐benzodithiolium perchlorate. Under rearomatization of the central frame protonation of 4 yields the salt 4c. The reaction of 4 with dicyanoketene gives the ‘push‐pull‐substituted’ 5, and with 9‐carbonylfluorene the fulvalene derivative 7, which can be protonated by CF3CO2H at C(9″) to the salt 8. The reaction of 2‐methylthio‐l,3‐dithiolium jodide 9 with the keto‐enol mixture 2 yields 10, which, on protonation at the carbonyl group by CF3CO2H, gives the salt 11 under rearomatization. The spectral data of the new compounds 4, 4c, 5, 7, 8, 10 and 11 are reported and discussed.

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Fulvenes and Fulvalenes of a Heterocyclic System with 12π Electrons—Pseudophenafulvenes and Pentapseudophenafulvalenes

Abstract: Heterocyclic fulvenes and fulvalenes iso‐π‐electronic with phenafulvenes and phenafulvalenes have now been prepared. One example is the dark blue crystalline fulvalene (1).

Cited by 6 publications

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Eine einfache Synthese substituierter Thiapseudo‐phenalenone

Eine einfache Synthese substituierter Thiapseudo‐phenalenone

Heterocyclische 12‐π‐ und 14‐π‐Systeme, XIX: Synthesen und Reaktionsverhalten von Thia‐pseudophenafulvenen und Thia‐pentapseudophenafulvalenen

Synthesen und chemische Eigenschaften neuer «Donor‐Akzeptor»‐stabilisierter Molekülsysteme mit zentraler Bicyclo [4.4.1]undeca‐l (10), 3,6,8‐tetraen‐2,5‐diyliden‐Gruppe

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