Preparation and reactivity of cyclodec-2-yn-1-one

Synthesis

Volumn , Issue 1, 1998, Pages 63-66

  Robertson, Jeremy ^a   Burrows, Jeremy N ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Diels Alder reaction of 2 cyclodecynone is described; Isomerisation; The preparation

Indexed keywords

ALKYNE DERIVATIVE; CYCLOALKANE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031963764     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2003     Document Type: Article

References (27)

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20. The strain in the nine- and ten-membered 2-ynones is reflected in the bond angles at C3 and C2 for the global minimum conformations obtained by Monte Carlo MM3* conformational searches. MacroModel v5.5: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulfied, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. These are respectively: for cyclonon-2-yn-1-one, 164 and 168°; for cyclodec-2-yn-1-one (1), 171 and 171°. The higher homologue, cycloundec-2-yn-1-one, is essentially angle-strain free with corresponding bond angles of 177°.
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