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Zur Kenntnis des Kohlenstoffringes. 81. Mitteilung [1]. Acetolyse des 3,3,8,8‐Tetramethyl‐cyclodecyl‐ p ‐toluolsulfonates
Author(s) -
Prelog V.,
Troxler E.,
Westen H. H.
Publication year - 1968
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.19680510723
Subject(s) - chemistry , medicinal chemistry , reaction rate constant , hydride , stereochemistry , organic chemistry , kinetics , metal , physics , quantum mechanics
Acetolysis of 3,3,8,8‐tetramethyl‐cyclodecyl p ‐toluenesulfonate yields 3,3,8,8‐tetramethyl‐ trans ‐cyclodecene‐(1) ( 6 ), 4,4,9,9‐tetramethyl‐ cis ‐cyclodecene‐(1) ( 4 ), and 4,4,9,9‐tetramethyl‐ trans ‐cyclodecene‐(1) ( 5 ). In each case 12 to 13 per cent of the product involves transannular hydride shifts. The rate constant k 25 = 4,35 · 10 −5 s −1 is approximately the same as for cyclodecyl p ‐toluenesulfonate. The reaction is discussed in terms of conformational analysis.