Fragmentation of 2-benzyl-3-(tosylazo) cyclohex-2-en-1-one to methyl 7-phenyl-5-heptynoate

R Friary, V Seidl

Index: Friary, R.; Seidl, V. Journal of Organic Chemistry, 1986 , vol. 51, # 16 p. 3214 - 3215

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Citation Number: 8

Abstract

Known reactions changed 2-benzyl-1, 3-cyclohexanedione'to 1.(Toluenesulfony1) hydrazine condensed with the dione forming 3 (16%): and HI04 oxidized 3 to the unstable 1 (92%). 4 The geometry of azo group substituents of 1 is presumably trans. 4 Such an arrangement would facilitate concerted Grob fragmentation of presumptive intermediate 4 (vide infra). 6i7