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[2 + 2]-Cycloadditions to Strained Bridgehead Olefins. II. Diphenylketene

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

Book ID
102251768
Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
446 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€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 and 10, respectively, in which the diphenylโ€substituted Cโ€atom is bound to the bridgehead. The structure of the cyclobutanone 8 has been determined by Xโ€ray analysis of a twin crystal obtained by crystallization with spontaneous enrichment of enantiomers.

๐Ÿ“œ SIMILAR VOLUMES

[2 + 2]-Cycloadditions to Strained Bridg
[2 + 2]-Cycloadditions to Strained Bridgehead Olefins. I. 1, 1-Dichloro-2,2-difluoroethene
โœ Konrad B. Becker; Martin K. Hohermuth ๐Ÿ“‚ Article ๐Ÿ“… 1982 ๐Ÿ› John Wiley and Sons ๐ŸŒ German โš– 368 KB

## 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

[2+2]- and [4+2]-Cycloadditions of Aryla
[2+2]- and [4+2]-Cycloadditions of Arylazoalkenes to Diphenylketene
โœ Dr. Sven Sommer ๐Ÿ“‚ Article ๐Ÿ“… 1977 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 203 KB ๐Ÿ‘ 1 views

Table 1 1.1 -Dichloro olefms (2) rrom 2,2,2-trichloroethanols ( I ) By-products 2,2-dichloroethanols ( 3 ) For conditions, see Procedure

Kinetics of 2+2 cycloadditions of diphen
Kinetics of 2+2 cycloadditions of diphenylketene to enol ethers; The structure of the orientation complexes
โœ Rolf Huisgen; Herbert Mayr ๐Ÿ“‚ Article ๐Ÿ“… 1975 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 208 KB

## Diphenylketene combines stereospecifically with @-and tmns-propenyl propyl ether to produce 4-methyl-2,2diphenyI-3-propoxy-cyclobutanones ; the cis'enol ether reacts 170 times faster than the tmns isomer. ' This impressive cis preference was later observed in further ketene cycloadditions, 2-5