Radical-chain addition of benzenethiol to allenes. Analysis of steric effects and reversibility

DJ Pasto, SE Warren, MA Morrison

Index: Pasto, Daniel J.; Warren, Steven E.; Morrison, Marjorie A. Journal of Organic Chemistry, 1981 , vol. 46, # 14 p. 2837 - 2841

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Citation Number: 35

Abstract

Results Addition of Benzenethiol to Monoalkylallenes. tert-Butylallene. The reaction of a slight excess of benzenethiol with tert-butylallene (la) at 25 OC in the absence of solvent resulted in the rapid, quantitative formation (by NMR) of a mixture of the adducts 2-5 in a 2017: 38: 25 ratio (eq 1). No 2: l adducts were indicated to be present by NMR and GC/MS. Adducts 2 and 5 were obtained pure by preparative GLC. Adducts 3 and 4 could not be ...

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