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Über Umlagerungen bei der Cyclialkylierung von Arylpentanolen zu 2,3‐Dihydro‐1 H ‐inden‐Derivaten, 4. Mitteilung
Author(s) -
Fathi Behrouz,
Giovannini Edgardo
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200207)85:7<2083::aid-hlca2083>3.0.co;2-#
Subject(s) - chemistry , medicinal chemistry
On Rearrangements by Cyclialkylations of Arylpentanols to 2,3‐Dihydro‐1 H ‐indene Derivatives. Part 4. The Acid‐Catalyzed Cyclialkylation of 2,4‐Dimethyl‐2‐phenyl[3‐ 13 C]pentan‐3‐ol The cyclialkylation of 2,4‐dimethyl‐2‐phenyl[3‐ 13 C]pentan‐3‐ol ( 4 ) gives only 2,3‐dihydro‐1,1,2,3‐tetramethyl‐1 H ‐[3‐ 13 C]indene ( 6 ) ( cf. Scheme 2 ) and not a trace of the isotopomeric 2,3‐dihydro‐1,1,2,3‐tetramethyl‐1 H ‐[2‐ 13 C]indene ( 5 ). The mechanism proposed in [3] for the cyclialkylation of 4 ( cf. Scheme 2, Path A ) has, therefore, to be abandoned. The mechanism of Scheme 2, Path B , is proposed and may be considered as definitively established.