RELATIVE RATES OF CYCLOAROMATIZATION OF DYNEMICIN AZABICYCLO[7.3.1]ENEDIYNE CORE STRUCTURES - AN UNUSUAL CHANGE IN DELTA-S(+ +)/

Authors
MAGNUS P FAIRHURST RA
Citation
P. Magnus et Ra. Fairhurst, RELATIVE RATES OF CYCLOAROMATIZATION OF DYNEMICIN AZABICYCLO[7.3.1]ENEDIYNE CORE STRUCTURES - AN UNUSUAL CHANGE IN DELTA-S(+ +)/, Journal of the Chemical Society, Chemical Communications, (13), 1994, pp. 1541-1542
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
13
Year of publication
1994
Pages
1541 - 1542
Database
ISI
SICI code
0022-4936(1994):13<1541:RROCOD>2.0.ZU;2-4
Abstract
A series of dynemicin core azabicyclo[7.3.1]enediynes undergo cycloaro matization at dramatically different rates despite the fact that the d istance (r, by X-ray diffraction) between the bonding acetylenes is pr actically identical (3.4 Angstrom); when the carbamate protecting grou p is removed to give the sec-amine 10, it cycloaromatizes more rapidly , and the entropy of activation changes from a negative to positive.