Abstract
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.
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