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Chemical and Spectroscopical Properties of Medium Sized trans ‐ and cis ‐Bicyclo[ n .1.0]alk‐2‐ynes
Author(s) -
Detert Heiner,
Meier Herbert
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970737
Subject(s) - chemistry , cyclopropane , ring strain , ring (chemistry) , triple bond , trifluoromethanesulfonate , ring size , reactivity (psychology) , bicyclic molecule , chemical shift , carbon 13 nmr , strain (injury) , stereochemistry , double bond , polymer chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Chemical and spectroscopical properties of cis ‐ and trans ‐cyclopropano‐anellated cycloalkynes of medium ring size are investigated and compared with results from force field calculations. IR and 13 C‐NMR data of the alkynes reflect the deformation of the triple bond due to ring strain. Parallel to bending the reactivity increases with decreasing ring size, the trans fused alkynes prove to be nearly as reactive as the cis fused with a two carbon smaller ring size. The bicycloalkynes are complexed with silver triflate. 13 C NMR reveals that the triple bond as well as the cyclopropane serve as ligands.