On the Base Catalyzed Cyclization of 2-Alkyl-2-P-Toluenesulfonoxymethylcyclohexanones

Wiberg, Kenneth B.; Klein, Gerald W.

doi:10.1016/b978-1-4831-9886-6.50211-4

Cited by 6 publications

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“…3-4-Hz spacing, 1, Hi or Hs), 2.0-0.8 (m, 6, methylenes), and 1.00 (s, 9, C(CH3)3). Further confirmation of the structural assignment was gained by photoisomerization of 16 (vide infra).…”

Section: Methodsmentioning

confidence: 96%

“…Vpc analysis of the original central fraction on the silver nitrate column (column B, 45°) showed it to consist of two fractions in a 60:40 ratio. These were readily separated under these conditions and the more rapidly eluting isomer was found to be 2-/m-butyl-I, 3-cycloheptadiene (16) as revealed by its pmr spectrum and photoisomerization to 15 (vide infra). The less dominant substance has been tentatively assigned structure 17 from pmr and ir data.…”

Section: Methodsmentioning

confidence: 99%

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Silver(I) ion catalyzed rearrangements of strained .sigma. bonds. XX. Substituent effects on the generation, structural rearrangement, and deargentation of argento carbonium ions. Kinetic and product study of the silver(I)-catalyzed isomerization of C1-functionalized tricyclo[4.1.0.02.7] heptanes

Paquette¹,

Zon²

1974

J. Am. Chem. Soc.

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203formed from the nine-membered ring case examined earlier. The products from 10t and its alcohol were the same as for the cis cases except that the ratio of 12c and 12t was approximately reversed. The spectra of the products are listed below. and 905 cm-l; nmr (6, CCla) 5.57 (m, l), 4.91 (d, J = 18 Hz, 11, 4.86 (d, J = 8 Hz. I), 1.2-2.6 (m, 17); massspectrummle 180.151 (calcdmlefor C I~H~~O , 180.151).Dodeca-l,ll-dien-3-one: nmr (6, CCh) 5.5-6.4 (m, 4), 4.7-5.1 (m, 2),2.3-2.6(m, 2), 1.9-2.3 (m, 2),and 1.1-1.8(m, 10).Kinetic Experiments. A series of ampoules were heated in either a fused salt bath maintained by a Bailey Model 124 proportional controller or in an aluminum block oven regulated by a Cole Palmer Model 1300 proportional controller. All runs for 1Oc used the fused salt bath. The runs for 10t used both and it was established that both devices gave the same rate at the same measured temperature, Each sample was hydrolyzed16 and analyzed on columns D and E. The data were treated as before. Acknowledgment.We thank Research C o r p o r a t i o n cis-Cyclodec-5-en-1-one (12c):for Cottrell Research Grant s u p p o r t .cis-Cyclodec-3-en-1-one. Oxidation3 of cis-cyclodec-3-en-1-01 gave a 62% yield of the desired ketone: ir (neat)

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“…3-4-Hz spacing, 1, Hi or Hs), 2.0-0.8 (m, 6, methylenes), and 1.00 (s, 9, C(CH3)3). Further confirmation of the structural assignment was gained by photoisomerization of 16 (vide infra).…”

Section: Methodsmentioning

confidence: 96%

Section: Methodsmentioning

confidence: 99%