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[2 + 2]-Cycloadditions to Strained Bridgehead Olefins. I. 1, 1-Dichloro-2,2-difluoroethene

โœ Scribed by Konrad B. Becker; Martin K. Hohermuth

Book ID
102251767
Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
368 KB
Volume
65
Category
Article
ISSN
0018-019X

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โœฆ Synopsis

Abstract

The strained bridgehead olefins bicyclo [3.3.1]nonโ€1โ€ene (1), bicyclo [4.2.1] nonโ€โ€1โ€(8) (2), and bicyclo [4.2.1]nonโ€1โ€ene (3) react rapidly with 1,1โ€dichloroโ€2, 2โ€โ€difluoroethene (5) to yield mixtures of regioisomeric dichlorodifluorocyclobutanes 8/9, 10/11 and 12/13, respectively. On the contrary, the reaction of 5 with the model compound (E)โ€lโ€methylcyclooctene (4) is completely regioselective. The structure of the cycloadducts has been elucidated mainly by ^19^Fโ€NMR. and ^13^Cโ€NMR. spectroscopy.

๐Ÿ“œ SIMILAR VOLUMES

[2 + 2]-Cycloadditions to Strained Bridg
[2 + 2]-Cycloadditions to Strained Bridgehead Olefins. II. Diphenylketene
โœ Konrad B. Becker; Martin K. Hohermuth; Grety Rihs ๐Ÿ“‚ Article ๐Ÿ“… 1982 ๐Ÿ› John Wiley and Sons ๐ŸŒ German โš– 446 KB

## Abstract The strained bridgehead olefins bicyclo [3.3.1]nonโ€1โ€ene (**1**), bicyclo [4.2.1 ]nonโ€1(8)โ€ene (**2**), and bicyclo [4.2.1]nonโ€1โ€ene (3), and the comparable monocyclic (__E__)โ€1โ€methylcyclooctene (**4**) react with diphenylketene (**6**) to give a single cycloadduct **7**, **8**, **9**