Issue 1, 2002
From the journal:

Chemical Communications

Novel reactions of phosphorus(iii) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion†

Sudha Kumaraswamy,a   Praveen Kommana,a   N. Satish Kumara  and  K. C. Kumara Swamy*a  

* Corresponding authors

a School of Chemistry, University of Hyderabad, Hyderabad-, India
E-mail: kckssc@uohyd.ernet.in
Fax: +91-40-3010120

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[triple bond, length as m-dash]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).

Graphical abstract: 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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Article information

DOI
https://doi.org/10.1039/B107087H
Article type
Communication
Submitted
10 Aug 2001
Accepted
06 Nov 2001
First published
03 Dec 2001

Chem. Commun., 2002, 40-41

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Novel reactions of phosphorus(III) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion

S. Kumaraswamy, P. Kommana, N. Satish Kumar and K. C. Kumara Swamy, Chem. Commun., 2002, 40 DOI: 10.1039/B107087H

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