A novel borane effect on the C/O alkylation ratio in competing SRN1-SN2 reactions

Ana Shifman, Milon Sprecher, Shmaryahu Hoz

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5 Scopus citations

Abstract

The presence of Et3B in the reaction of 2-nitropropane anion (1) with p-nitrobenzyl bromide (5b) in tert-butyl alcohol results in an approximately three-fold increase in C-alkylation [yielding 1-(2-methyl-2-nitropropyl)-4-nitrobenzene (9) by an SRN1 mechanism] versus O-alkylation (by an SN2 mechanism, and leading thereafter to p-nitrobenzaldehyde). Dioxygen completely inhibits C-alkylation in the absence of Et3B, but is ineffective in its presence. p-Dinitrobenzene does not significantly affect the thermal reaction (30°C) of 1 with 5b, but partially inhibits C-alkylation in reaction under photostimulation. However, p-dinitrobenzene catalyzes C-alkylation in the thermal reaction in the presence of Et3B. Rationalizations of these novel results are presented. Qualitatively similar results were obtained for the reaction of phenylnitromethane anion (16) with 5b.

Original languageEnglish
Pages (from-to)105-111
Number of pages7
JournalJournal of Physical Organic Chemistry
Volume13
Issue number2
DOIs
StatePublished - Feb 2000

Keywords

  • Borane effect
  • C/O alkylation ratio
  • S1-S2 reactions

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