Novel reactions of phosphorus(iii) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion
2002
Kumaraswamy, Sudha | Kommana, Praveen | Satish Kumar, N. | Kumara Swamy, K. C.
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 MeO₂CCCCO₂Me; 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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