Secondary and tertiary 2-methylbutyl cations. 1. Trifluoroacetolysis of 3-methyl-2-butyl tosylate

D Farcasiu, G Marino, JM Harris…

Index: Farcasiu, Dan; Marino, Gaye; Harris, J. Milton; Hovanes, Bruce A.; Hsu, Chang S. Journal of Organic Chemistry, 1994 , vol. 59, # 1 p. 154 - 162

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Citation Number: 14

Abstract

Trifluoroacetolysis rates for 3-methyl-2-butyl tosylate (4) and kinetic isotope effects at C (1)(kH/kD= 1.083 per H atom), C (2)(k~/k~= l. lO), and C (3)(kdkD= 1.82) were determined. The products are 2-methyl-2-butyl trifluoroacetate (5, 98.5%) and 3-methyl-2-butyl trifluoroacetate (6, 1.5%). GC-MS analysis of products from labeled tosylates 4-14 and 4-2-d showed that 42% of the apparently unrearranged 6 had a methyl group shifted from the ...