2‐(Phenylsulfonyl)‐1,3‐cyclohexadiene

Abstract

2‐(Phenylsulfonyl)‐1,3‐cyclohexadiene intermediate: trans‐3‐(phenylsulfonyl)‐4‐(chloromercuri)cyclohexene product: 2‐(phenylsulfonyl)‐1,3‐cyclohexadiene

Economical and Environmentally Friendly Syntheses of 2-(Phenylsulfonyl)-1,3-cyclohexadiene and 2-(Phenylsulfonyl)-1,3-cycloheptadiene1

“…The oil was diluted with diethyl ether (10 mL) and placed in a −30 °C freezer. One crystallization of the oil provided 30.71 g (89%) of 1 as white crystals: mp 58−61 °C (lit . 60−63 °C); R f 0.53 (1:1 v/v ethyl acetate/hexane); 1 H and 13 C NMR agree with literature; 13 C NMR (125 MHz, CDCl 3 ) δ 20.54, 22.06, 118.17, 127.46, 128.96, 129.87, 133.06, 134.64, 138.45, 139.67.…”

“…When this research was in its infancy, two simple and efficient methods by Bäckvall provided ample amounts of material for initial experiments. Bäckvall's synthesis of 2-(phenylsulfonyl)-1,3-cyclohexadiene 1 involves a phenylsulfonylmercuration of 1,3-cyclohexadiene followed by the β-elimination of mercury(0) to form the 2-phenylsulfonyl-substituted diene . The synthesis of 2-(phenylsulfonyl)-1,3-cycloheptadiene 2 is accomplished by a tandem selenosulfonation-oxidation of 1,3-cycloheptadiene with phenyl benzeneselenosulfonate.…”

Organocatalytic Asymmetric 1,6‐Addition Reactions

“…In 1999, Hentemann et al. presented a new route to synthesize sulfonated cyclohexadiene‐ trans ‐diols (e.g., 73 ) from cyclohexa‐1,3‐diene ( 74 ) via stereoselective epoxidation of, e.g., cyclohexa‐1,3‐diene‐2‐sulfonates ( 75 ) (synthesized via 76 ),21 furnishing epoxide 77 (Scheme ) 22,23. Subsequent ring‐opening towards silyl ether 78 followed by another round of epoxidation and ring‐opening led to the sulfonated cyclohexadiene‐ trans ‐diols ( 73 via 79 ).…”