1969
DOI: 10.1021/jo01263a075
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New Friedel-Crafts chemistry. XIX. Cyclialkylations of some phenylalkanols

Abstract: CYCLIALKYLATIONS OF SOME PHENYLALKANOLS 3571 ratio was detected until the amount of olefin exceeded 10%. Above 10% small differences were noted and the values indicated that the cis alcohol (equatorial OH) was being dehydrated a t a faster rate than the trans alcohol.Control Experiment.--The isolated product obtained from the reaction of methylmagnesium bromide (0.1 M ) with 4-t-butylcyclohexanone (Table I) was dissolved in 10 ml of ether and added to dimethylcadmium or dimethylzinc reagents under the conditio… Show more

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Cited by 20 publications
(4 citation statements)
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“…molecular weight compounds via tertiary carbocationic species were also reported in Friedel-Crafts chemistry. 14 The methyl substituent in the isoprene unit would also contribute to more effective cyclization due to the formation of sterically favored 6-endo-trig-like conformation.…”
Section: Cationic Cyclization Of Various R-sir Analoguesmentioning
confidence: 99%
“…molecular weight compounds via tertiary carbocationic species were also reported in Friedel-Crafts chemistry. 14 The methyl substituent in the isoprene unit would also contribute to more effective cyclization due to the formation of sterically favored 6-endo-trig-like conformation.…”
Section: Cationic Cyclization Of Various R-sir Analoguesmentioning
confidence: 99%
“…The procedures described earlier for cyclialkylations of arylalkanols with AlCl 3 /CH 3 NO 2 and PPA were essentially followed. The conditions and yields are shown in Tables and , whereas the physical constants and spectral data of the products 8a , 8b , 8c , 8d , 8e , 8f , 8g , 8h , 8i are given in the following.…”
Section: Methodsmentioning
confidence: 99%
“…Despite numerous advances in the field of synthetic organic chemistry, the developments of valuable and efficient strategies for the construction of these ring systems remain as a significant challenge. Among these methods, intramolecular Friedel–Crafts cyclialkylations promoted by both Brønsted and Lewis acid catalysts is promising as an efficient method to prepare substituted julolidines.…”
Section: Introductionmentioning
confidence: 99%
“…1 (4) The formation of 6 via intermediates 5 finds analogy in an earlier paper co-authored by one of us. 4 Experimental IR spectra were recorded on a Nicolet Magna 520 FT-IR spectrometer, 1 H NMR spectra were recorded on a Bruker DPX-400 FT-NMR spectrometer, GC-MS data were obtained with a Shimdazu QP-5000 mass spectrometer and microanalyses were performed on a 2400 Perkin Elmer Series 2 CHNS analyser.…”
mentioning
confidence: 99%