SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 47. REGIOSELECTIVITY, STEREOSELECTIVITY AND KINETICS OF [2+3]CYCLOADDITION REACTION OF <i>Z</i>-C,N-DIPHENYLNITRONE WITH <i>E</i>-β-NITROSTYRENES

Authors

  • A. Baranski Krakow University of Technology, 31-155 Krakow
  • R. Jasinski Krakow University of Technology, 31-155 Krakow

Keywords:

nitroalkenes, nitroisoxazolidines, nitrones,, [2+3]cycloaddition, regioselectivity, stereoselectivity, substituent effect

Abstract

The [2+3]cycloaddition of Z-C,N-diphenyinitrone with E-(β-nitrostyrenes leads to (3SR, 4SR, 5SR- and (3SR, 4RS, 5RS)-2,3-diphenyl-4-nitro-5-aryliso-xazolidines as the only reaction products. The kinetics of the reaction was studied by using the HPLC method. It was found that total rate constants increase with increasing substituent Hammett α-constants. The substituent effect is rationalised in terms of FMO theory.

How to Cite
Baranski, A.; Jasinski, R. Chem. Heterocycl. Compd. 2001, 37, 1518. [Khim. Geterotsikl. Soedin. 2001, 1670 .]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1014509310331

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Published

2001-12-25 — Updated on 2024-11-14

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Issue

No. 12 (2001)

Section

Original Papers