Effect of aggregation of nitrile anions on the 1,2 versus 1,4 regioselectivity towards benzylideneacetone

DOI: 10.1016/S0040-4039(00)76706-2

Source and publish data:

Tetrahedron Letters p. 3935 - 3936 (1994)

Update date:2022-08-05

Topics:

Authors:

Strzalko

Seyden-Penne

Wartski Wartski

Froment Froment

Corset Corset

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Article abstract of DOI:10.1016/S0040-4039(00)76706-2

A direct evidence of the influence of aggregation state of lithiated penylacetonitrile 1 on the 1,2 versus 1,4 regioselectivity towards benzylideneacetone 2 was established. Progressive addition of hexane to THF solutions raised the aggregates proportion of 1 as evidenced by IR ν(CN) band and led to an increase of 1,4 adduct. Monomers afforded 1,2 addition in pure THF.

Full text of DOI:10.1016/S0040-4039(00)76706-2

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