Novel reactions of phosphorus(III) azides and isocyanates: Unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion
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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Date
2002-01-01
Authors
Kumaraswamy, Sudha
Kommana, Praveen
Satish Kumar, N.
Kumara Swamy, K. C.
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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)N[NP(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≡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). © 2002 The Royal Society of Chemistry.
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Chemical Communications. v.2(1)