Stereospecificity in hydrogen atom transfer to the vinyl radicals derived from the cis- and trans-tert-butyl .alpha.-chloropercinnamates

Azaenolates of 2-Chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline − A Highly Diastereo- and Enantioselective Synthesis of Oxazolinyloxiranes

“…In contrast, the reaction of the tin azaenolate 11 (Scheme ), generated upon treatment of oxazoline 1 with Sn(OTf) 2 and diisopropylethylamine (DIPEA) in THF at room temperature, with PhCHO furnished the Z ‐chloro(oxazolinyl)styrene 12 (50% yield),16 while the reaction of 11 with benzophenone and cyclohexanone led to the oxazolinyloxiranes 13 and 14 , respectively, with excellent stereoselectivity (80%, dr = 97:3; 75%, dr = 96:4).…”

Thermal decomposition of tert-butyl ortho-(phenylsulfanyl)- and ortho-(phenylsulfonyl)phenyliminoxyperacetates: The reactivity of thio-substituted iminyl radicals

“…The organic phase was dried, the solvent was removed, and the residue recrystallised from light petroleumbenzene mixtures. (8), 184 (16), 134 (10), 109 (29), 77 (29) and 51 (21). (17), 77 (14) and 51 (12).…”

“…oxy]peracetate 7a. Starting from 6a (6.5 g, 22.7 mmol), perester 7a was obtained (6.5 g, 80%) as an oil; δ H (200 MHz) 1.20 (9 H, s, tert-Bu), 4.65 (2 H, s, CH 2 ), 7.05-7.30 (8 H,m, (1 H, m, Ar-H) and 8.65 (1 H, s, N᎐ ᎐ CH); m/z 315 (M ϩ Ϫ 44, 10%), 285 (15), 229 (17), 212 (97), 197 (13), 184 (23), 136 (15), 109 (17), 77 (23), 57 (100) and 51 (21).…”

“…From 7a. Perester 7a (15 mmol) gave, in order of elution, 2-(phenylsulfanyl)benzaldehyde O-(tert-butyl)oxime 11a (0.26 g, 6%) as an oily 6 : 1 mixture of geometric isomers; δ H (200 MHz) 1.32 (0.14 × 9 H,s,minor isomer),1.35 (0.86 × 9 H,s,major isomer),m, (10), 212 (77), 184 (23), 109 (16), 77 (25) m,m,m, (1 H, m, Ar-H); m/z 211 (M ϩ , 100%), 210 (34), 184 (41), 109 (11), 77 (43) 17.38, 119.79, 123.35, 124.45, 127.46, 135.01, 152.00 and 162.79 [lit., 24 δ C 17.39, 119.49, 123.36, 124.44, 127.43, 135.03, 152.03 and 162.80 (10), 228 (34), 226 (72), 213 (57), 184 (24), 77 (21) and 57 (100); ketone 4b (0.56 g, 16%); oxime 5b (0.35 g, 10%).…”

“…m, (2 H, m, Ar-H) (N-H non-visible); m/z 289.0920 (M ϩ , 21%. C 19 H 15 NS requires M, 289.0925), 288 (6), 212 (100), 184 (8), 109 (21) and 77 (36); ketone 4c (0.47 g, 11%); oxime 5c (0.18 g, 4%).…”