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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
Author(s) -
FranckNeumann Michel,
Miesch Michel,
Gries Stefan,
Irngartinger Hermann
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201136
Subject(s) - chemistry , substituent , cycloaddition , medicinal chemistry , crystal structure , propenyl , benzene , stereochemistry , pentane , crystallography , organic chemistry , catalysis
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.