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Chemische Verschiebungen bei 17 O‐NMR. und Hydratations geschwindigkeiten von cyclischen Ketonen mit transannularer Wechselwirkung
Author(s) -
Dahn H.,
Schlunke H.P.,
Temler J.
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550316
Subject(s) - chemistry , medicinal chemistry , carbonyl group , oxygen atom , stereochemistry , organic chemistry , molecule
Abstract In 8‐ and 9‐membered cyclic ketones, transannular interactions of an EtN group or an O atom shift considerably the 17 O signal of the carbonyl group to higher fields; S appears to have no such effect. The same ketones show markedly diminished speeds of water addition, compared to simple ketones; this reaction was followed by measuring the rate of oxygen exchange between 17 O‐labelled ketones and (unenriched) water. Transannular interaction inhibits completely in N‐ethyl‐azacyclodecane‐6‐one the exchange reaction, including labelling attemps.