α-Sulfinyl carbenoid: One-carbon homologation of ketones to α-sulfinyl ketones using chloromethyl phenyl sulfoxide

Satoh, Tsuyoshi; Hayashi, Yasumasa; Mizu, Yasuhiro; Yamakawa, Kōji

doi:10.1016/s0040-4039(00)60867-5

Cited by 24 publications

(6 citation statements)

References 20 publications

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“…1 3 12)), 26.40 (t), 26.27 (t), 23.82 (t), 22.79 (t), 22.53 (t), 22.41 (t), 21.68 (t, C(11)), 19.55 (t, C(4)). EI-MS: 224 (7, M +• ), 181 (9), 167 (7), 153 (8), 139 (9), 125 (14), 111 (27), 97 (32), 83 (95), 70 (56), 55 (100)…”

Section: -Hydroxy-2-vinylcyclododecanone (6a)mentioning

confidence: 99%

“…1 H NMR (300 MHz, CDCl 3 ) δ 5.24 (s, CH 2 (2')), 5.10 (s, CH 2 (2')), 4.29 (s, 1 H), 3.13-3.02 (m, 1 H), 2.22-2.11 (m, 2 H), 2.04-1.95 (m, 1 H), 1.91-1.80 (m, 1 H), 1.61 (s, CH 3 ), 1.62-1.49 (m, 1 H), 1.34-1.18 (m, 7 H), 0.84-0.72 (m, 1 H). 1 3 (7), 181 (9), 163 (10), 153 (8), 139 (13), 125 (19), 111 (33)…”

Section: -Hydroxy-2-isopropenylcyclododecanonementioning

confidence: 99%

“…1 3 4)), 13.63 (q, CH 3 (3')), 12.01 (q, CH 3 (1'')). EI-MS: 252 (6, M +• ), 234 (1), 224 (8), 209 (19), 195 (4), 181 (5), 167 (7), 139 (7), 125 (9), 111 (74), 98 (57), 83 (100), 69 (28), 55 (92).…”

Section: (E)-and (Z)-2-hydroxy-2-(1-methylprop-1-enyl)cyclododecanoneunclassified

“…1 3 C NMR (75 MHz, CDCl 3 ) δ 211.28 (s, C( 1)), 209.38 (s, C(1)), 130.39 (d), 130.07 (d), 128.27 (d), 124.12 (d), 83.37 (s, C( 2)), 81.63 (s, C( 2)), 36.71 (t), 36.22 (t), 35.45 (t), 31.64 (t), 31.42 (t), 24.48 (t), 24.23 (t), 24.12 (t), 24.04 (t), 23.92 (t), 21.43 (t), 20.66 (t), 20.50 (t), 20.44 (t), 20.26 (t), 20.16 (t), 20.12 (t), 19.44 (t), 18.00 (t), 17.57 (t), 17.56 (q, CH 3 ), 13.10 (q, CH 3 ), 0.47 (q, (CH 3 ) 3 Si), 0.35 (q, (CH 3 ) 3 Si). EI-MS: 310 (2, M +• ), 282 (11), 267 (9), 253 (3), 239 (6), 211 (5), 197 (17), 169 (78), 157 (15), 130 (33), 115 (3), 73 (100), 55 (28). Anal.…”

Section: (E/z)-2-(prop-1-enyl)-2-trimethylsilyloxycyclododecanone (10d)mentioning

confidence: 99%

“…1 3 C NMR (75 MHz, CDCl 3 ) δ 211.55 (s, C( 1)), 146.53 (s, C(1')), 113.54 (t, C(2')), 88.14 (s, C( 2)), 35.23 (t), 33.65 (t), 27.17 (t), 26.41 (t), 23.86 (t), 23.12 (t), 23.06 (t), 22.71 (t), 21.64 (t), 20.96 (t), 19.79 (q, CH 3 ), 2.79 (q, (CH 3 ) 3 Si). EI-MS: 310 (3, M +• ), 295 (11), 282 (7), 253 (4), 239 (5), 211 (3), 183 (9), 169 (38), 144 (71), 95 (7), 73 (100), 55 (28). Anal.…”

Section: -Isopropenyl-2-trimethylsilylcyclododecanone (10f)mentioning

confidence: 99%

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Diradical‐Promoted (n + 2 ‐ 1) Ring Expansion: An Efficient Reaction for the Synthesis of Macrocyclic Ketones.

Rüedi¹,

Oberli²,

Nagel³

et al. 2004

ChemInform

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Synthesis of Macrocyclic Ketones. -A conceptually new ring expansion reaction provides access to specifically substituted cycloalkanones in good yields. The substituted vinyl substrates are transformed regiospecifically. The by-products arise from a decarbonylation reaction. 2-Ethynyl derivative (XIII) reacts in a similar manner to give a mixture of (E)-and (Z)-ketones. -(RUEDI*, G.; OBERLI, M. A.; NAGEL, M.; HANSEN, H.-J.; Org. Lett. 6 (2004) 18, 3179-3181; Org.-Chem. Inst., Univ. Zuerich, CH-8057 Zuerich, Switz.; Eng.) -Steudel 51-063

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Section: -Hydroxy-2-vinylcyclododecanone (6a)mentioning

confidence: 99%