The Journal of Organic Chemistry

A useful method of optical activity. IX. Determination of the absolute configuration of a spiro quaternary ammonium salt via Stevens rearrangement

JH Brewster, RS Jones Jr

Index: Brewster,J.H.; Jones,R.S. Journal of Organic Chemistry, 1969 , vol. 34, # 2 p. 354 - 358

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Citation Number: 23

Abstract

Toluene 136 2-Methylanisole 133 3-hlethylanisole 137 2, 3-Dimethylanisole 134,130 groups (ArCH, N+) give sharp singlets at different positions in tetrahydroisoquinolinium and isoindolinium salts (6 4.65 and 4.95, respectively). Thus positions 7 and 5 should be distinguishable in the methiodide of any of the four positional isomers. The presence of an o- methoxy group has an appreciable shielding effect in the spiro salt 2b (Table I) and in the ...

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