ISSN:
0009-2940
Keywords:
(1-Diazo-2-oxoalkyl)silanes
;
Cyclopropenes
;
Cycloaddition
;
Silyl shift
;
Homopyrazole
;
1,4-Dihydropyridazine isomerization
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(1-Diazo-2-oxoalkyl)silanes 1a-h react with cyclopropene 4 to form 2-silyl-2,3-diazabicyclo[3.1.0]hex-3-enes 5 and/or 1-silyll-1,4-dihydropyridazines 6. In most cases, a temperature- and solvent-dependent equilibrium 5 ⇄ 6 maintained by an N →N′ silyl shift exists in solution. With cyclopropene 10, only the 1-silyl-1,4-dihydropyridazines 11 are obtained. None of the 1:1 adducts corresponds to the product expected from a [3 + 2] cycloaddition reaction between the components. Evidence is presented that 1-diazo-2-siloxy-1-alkenes 2 are initially formed from 1 by a 1,3-(C → O) silyl shift and are then trapped by the cyclopropene in a 1,3-dipolar cycloaddition reaction.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250532
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