TY - JOUR
T1 - Competitive [4 + 2]-Cycloaddition versus [1,5]-Hydrogen Sigmatropy in a Cycloheptatriene. An Efficient Route to 3-Azatricyclo[5.3.1.04,10]undeca-5,8-diene
AU - Krow, Grant R.
AU - Cannon, Kevin C.
AU - Carey, James T.
AU - Hong, Ma
AU - Ramesh, Raghavachari
AU - Szczepanski, Steven W.
PY - 1988/10/1
Y1 - 1988/10/1
N2 - Thermal rearrangements of N-acyl-7-aminocyclohepta-1,3,5-trienes 7b-e in octane or xylene provide [4 + 2]-cycloaddition products 8b-e and [1,5]-hydrogen sigmatropic rearrangement products 9b-e. The relative rate of formation for 8e/9e is 1.5 in refluxing octane. At a higher reaction temperature in xylene and longer reaction times, 7b afforded a second hydrogen-shift product 10b. No thermal [3,3]-carbon shift products were observed from IV-allyl cycloheptatrienes 9b-e or 10b in octane or xylene. The thermal behavior of 7b-e can be contrasted with that of O-allyl cyclohepta-1,3,5-triene 1.
AB - Thermal rearrangements of N-acyl-7-aminocyclohepta-1,3,5-trienes 7b-e in octane or xylene provide [4 + 2]-cycloaddition products 8b-e and [1,5]-hydrogen sigmatropic rearrangement products 9b-e. The relative rate of formation for 8e/9e is 1.5 in refluxing octane. At a higher reaction temperature in xylene and longer reaction times, 7b afforded a second hydrogen-shift product 10b. No thermal [3,3]-carbon shift products were observed from IV-allyl cycloheptatrienes 9b-e or 10b in octane or xylene. The thermal behavior of 7b-e can be contrasted with that of O-allyl cyclohepta-1,3,5-triene 1.
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U2 - 10.1021/jo00247a001
DO - 10.1021/jo00247a001
M3 - Article
AN - SCOPUS:4444312716
SN - 0022-3263
VL - 53
SP - 2665
EP - 2668
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 12
ER -