- Polycycles from 1,5-Cyclooctadiene and Chlorocyanoketene.
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Chlorocyanoketene adds to cyclohexene and cyclooctene stereoselectively to give 1 or 2; 1,5-cyclooctadiene, however, yields a four-component mixture of 3a, b and 4a, b.Cyclooctatetraene reacts with the ketene differently to yield 5.Favorskii reactions of 1-3 lead to bicyclic compounds carrying carboxylic groups at bridgehead carbons (6a,b;7a,b;8a,b).The diazoketones accessible from 6a or 6b, respectively, give C-H insertion products (13a,b) and intramolecular cyclopropanation products (14a,b) when decomposed in the presence of RhII.
- Dehmlow, Eckehard V.,Birkhahn, Michael
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p. 701 - 704
(2007/10/02)
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- Chlorocyanoketene. Synthesis and Cycloadditions to Alkenes
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Details for two syntheses of chlorocyanoketene (CCK) are provided.These involve the thermolysis (103 deg C) of 4-azido-3-chloro-5-methoxy-2(5H)-furanone as well as generation of the ketene at ambient temperature upon treatment of 3,4-dichlorocyclobutendio
- Fishbein, Paul L.,Moore, Harold W.
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p. 2190 - 2194
(2007/10/02)
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