Novel reactions of phosphorus(III) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion |
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Authors: | Kumaraswamy Sudha Kommana Praveen Kumar N Satish Swamy K C Kumara |
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Institution: | School of Chemistry, University of Hyderabad, Hyderabad-500046, A. P., India. |
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Abstract: | New modes of 1,3-dipolar cycloaddition are uncovered by the isolation of CH2(6-t-Bu-4-Me-C6H2O)2]P(C(CO2Me)C(CO2Me)NNP(N3)(OC6H2-6-t-Bu-4-Me)2CH2]N) (3) and CH2(6-t-Bu-4-Me-C6H2O)2]P(C(CO2Me)C(CO2Me)C(O)N) (4) on treating CH2(6-t-Bu-4-Me-C6H2O)2]P-X X = N3 (1) and NCO (2)] with the dipolarophile MeO2CC identical to CCO2Me; compound 4 undergoes an unprecedented ring expansion upon addition of 2-(methylamino)ethanol to afford the spirocycle CH2(6-t-Bu-4-Me-C6H2O)2]P(OCH2CH2N(Me)CH(CO2Me)CH(CO2Me)C(O)N) (5). |
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