2014
DOI: 10.1002/hc.21209
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Interaction of 1,3,2,4‐Benzodithiadiazines with Aromatic Phosphines and Phosphites

Abstract: Although an interaction between hydrocarbon and fluorocarbon 1,3,2,4‐benzodithiadiazines (1 ) and P(C6H5)3 continuously produces chiral 1,2,3‐benzodithiadiazol‐2‐yl iminophosporanes (2; in this work, 5,7‐difluoro derivative 2a ) via 1:1 condensation, an interaction between 1 and other PR3 reagents gives different products. With R  OC6H5 and both hydrocarbon and fluorocarbon 1, only X=P(OC6H5)3 (X = S, O) were identified in the complex reaction mixtures by 13С and 31Р NMR and GC‐MS. With R = C6F5, no interacti… Show more

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Cited by 9 publications
(2 citation statements)
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“…Such a rapid migration from S to N has been demonstrated previously for the reaction of phosphines with sulfur diimides . The reaction of Ph 3 P with 1,3,2,4‐benzodithiadiazines also results in the extrusion of a ring nitrogen atom to form an iminophosphorane substituent at sulfur in a smaller ring . Complete severance of the N1−S3 bond leads to the chain intermediates 3 (all atom numbers refer to usage in Figure ).…”
Section: Resultssupporting
confidence: 47%
“…Such a rapid migration from S to N has been demonstrated previously for the reaction of phosphines with sulfur diimides . The reaction of Ph 3 P with 1,3,2,4‐benzodithiadiazines also results in the extrusion of a ring nitrogen atom to form an iminophosphorane substituent at sulfur in a smaller ring . Complete severance of the N1−S3 bond leads to the chain intermediates 3 (all atom numbers refer to usage in Figure ).…”
Section: Resultssupporting
confidence: 47%
“…The type B RAs for 1 – 14 were also optimized. They featured tremendously elongated (by 0.546–0.762 Å) S1−X2 bond lengths (Table ), which assumes weakened or, more likely, bond breaking. The type B RAs have a σ*(S1−X2, X=S or Se) SOMO (see Figure for the RA of 9 ).…”
Section: Resultsmentioning
confidence: 99%