Cycloaddition eines sehr reaktiven Cyanovinylcarbens mit Benzol und 3,4-Dichlorcyclobuten Molekular- und Kristallstruktur von 2,3-Dichlor-5-(1-cyano-2-methyl-1-propenyl)-5-hausancarbonitril und 7-(1-Cyano-2-methyl-1-propenyl)-7-norcaradiencarbonitril
✍ Scribed by Franck-Neumann, Michel ;Miesch, Michel ;Gries, Stefan ;Irngartinger, Hermann
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 341 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Cycloaddition of a Very Reactive Cyanovinylcarbene with Benzene and 3,4‐Dichlorocyclobutene. Molecular and Crystal Structure of 2,3‐Dichloro‐5‐(1‐cyano‐2‐methyl‐1‐propenyl)‐5‐housanecarbonitrile and 7‐(1‐Cyano‐2‐methyl‐1‐propenyl)‐7‐norcaradienecarbonitrile
The cyanovinylcarbene 2 has been generated by photolysis of 3,3‐dimethyl‐3__H__‐pyrazole‐4,5‐dicarbonitril (1) and the cycloaddition products with benzene and with 3,4‐dichlorocyclobutene have been isolated. The molecular structures of the cycloaddition products 7‐(1‐cyano‐2‐methyl‐1‐propenyl)‐7‐norcaradienecarbonitrile (3) and 2,3‐dichloro‐5‐(1‐cyano‐2‐methyl‐1‐propenyl)‐5‐housanecarbonitrile (4) were determined by X‐ray analyses. The bridging bond of the bicyclo[2.1.0]pentane group in 4 is shortened to 1.515 Å by the electronic interaction of this group with the cyano substituent. The vinyl substituent has no influence because of perpendicular orientation.