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Organophosphorverbindungen, 73. Der Tri‐ tert ‐butyl‐2‐cyclopropen‐1‐yl‐Rest als kinetisch stabilisierende Gruppe für 1‐Aza‐3‐phosphaallene
Author(s) -
Wegmann Thomas,
Hafner Michael,
Regitz Manfred
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931261129
Subject(s) - chemistry , tautomer , hexamethyldisiloxane , bifunctional , substituent , medicinal chemistry , stereochemistry , organic chemistry , catalysis , physics , plasma , quantum mechanics
Organophosphorus Compounds, 73 [1] . – The Tri‐ tert ‐butyl‐2‐cyclopropen‐1‐yl Substituent as Kinetically Stabilizing Group for 1‐Aza‐3‐phosphaallenes [2] The cyclopropenylphosphane 5 reacts with the isocyanates 6a–g to form the phosphaalkenes 7a–g . An analogous transformation occurs with the same phosphane and the bifunctional isocyanates 8a, b (→ 9a, b) . In contrast, the reaction 5 + 6h ends at the stage of the tautomers 11h ⇆ 12h . Methanolysis of 7b and of 11h ⇆ 12h leads to the carbamoyl‐cyclopropenylphosphanes 14a and b , respectively. Sodium hydroxide‐catalyzed elimination of hexamethyldisiloxane from 7b, g and the tautomer mixture 11h ⇆ 12h yields the target 1‐aza‐3‐phosphaallenes 16a–c .