Vinyl cations. 41. Influence of 4-aryl and 4-alkyl substituents on the. pi.-route solvolyses of homopropargyl esters

CJ Collins, M Hanack, H Stutz, G Auchter…

Index: Collins, Clair J.; Hanack, Michael; Stutz, Herbert; Auchter, Gerhard; Schoberth, Winfried Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5260 - 5268

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Citation Number: 24

Abstract

The four 4-substituted-homopropargyl tosylates and triflates 6b-e (R= phenyl, p-tolyl, anisyl, and cyclopropyl) have been synthesized and solvolyzed under various conditions, as have 2- cyclopropyl-1-cyclobutenyl triflate (11-OTf) and nonaflate (11-ONf). In addition, the solvolyses of pent-3-yn-1-yl tosylate (6a-OTs, R= methyl) and triflate (prepared previously) are reported. The ratios of C-3 ring to C-4 ring [R (C3 ring/C, ring)] products are recorded ...

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