Reaction of (–)-menthyl(S)-toluene-p-sulphinate with nitriles and lithium NN-di-isopropylamide (LDA) in 1:1:1 and 1:2:1 ratios affords optically active α-cyano- and α-cyano-β-imino-sulphoxides, respectively. α-Cyanobenzyl sulphoxide racemizes through a homolytic process in a temperature range (35–50 °C) well below that required for benzyl aryl sulphoxides.
Synthesis and stereomutation of optically active alpha-cyanosulphoxides / R. Annunziata, M. Cinquini, S. Colonna, F. Cozzi. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :0(1981), pp. 614-617.
Synthesis and stereomutation of optically active alpha-cyanosulphoxides
R. AnnunziataPrimo
;M. CinquiniSecondo
;S. ColonnaPenultimo
;F. CozziUltimo
1981
Abstract
Reaction of (–)-menthyl(S)-toluene-p-sulphinate with nitriles and lithium NN-di-isopropylamide (LDA) in 1:1:1 and 1:2:1 ratios affords optically active α-cyano- and α-cyano-β-imino-sulphoxides, respectively. α-Cyanobenzyl sulphoxide racemizes through a homolytic process in a temperature range (35–50 °C) well below that required for benzyl aryl sulphoxides.
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