ISSN:
0009-2940
Keywords:
Phosphaalkyne, amino-
;
[3 + 2] Cycloaddition
;
1,2,4-Diazaphospholes
;
1,2,3-Diazaphospholes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reactive E = C(p - p)π Systems, XXXII[1]. - First Representatives of Amino-Substituted 1,2,4-Diazaphospholes(Diisopropylamino)phosphaethyne iPr2N - C≡P reacts at 20° C in a [3 + 2] cycloaddition with (trifluoromethyl)diazomethane (2a) or methyl diazoacetate (2b) to yield a mixture of the corresponding regioisomers 1H-1,2,4-diazaphospholes (5a or 5b) and 1H-1,2,3-diazaphospholes (6a or 6b) in quantitative yields (isomer ratio: 5a/6a = 2:1; 5b/6b = 4:1). X-ray diffraction studies on 5a and 5b indicate a delicate charge balance in the bonding system of 1H-1,2,4,σ2-diazaphospholes under the influence of the exocyclic push/pull substituents iPr2N and CF3 or CO2Me, respectively.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250219
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