Cyclodecanone, acidity

The procedure described is a modification of the directions of Prelog, Frenkiel, Kobelt, and Barman. Cyclodecanone has been prepared by the dehydration of sebacoin followed by catalytic hydrogenation, by the pyrolysis of the thorium or yttrium salt of nonane-1,9-dicarboxylie acid, and by the ring enlargement of cyclononanone, as well as by the reduction of sebacoin. ... 

Cyclodecanone has been obtained together with other products in the pyrolysis of the thorium or yttrium salts of nonanedioic acid.3 4 It has also been prepared by reduction of sebacoin with zinc and hydrochloric acid,6, 6 by dehydration of sebacoin fol-... 

Cyclobutanecarboxylic acid, reaction with hydrazoic add, 47, 28 Cyclobutene, 1,2,3,4-tetramethyl-3,-4-oichloro-, 46, 34 reactions of, 46, 36 Cyclobutylamine, 47,28 Cvclobutyl isocyanide, 46, 77 Cyclodecanone, 48, 56 Cyclododecanone, conversion to cyclo-tetradecanone, 48, 58 Cyclohcptanone, 45, 31 conversion to cyclononanone, 48, 58 1, 3-Cyclohexadiene, 47, 31... 

Oxotricyclo[6.5.0.02-7]tridecan-l-yl acetate 4 rearranged on heating to 110°C in benzene in the presence of p-toluenesulfonic acid to afford a bicyclic cyclodecanone derivative.231... 

Cupric acetate is also used for oxidations of acyloins. Diphenylacetoin is converted almost quantitatively into dibenzylglyoxal when refluxed with cupric acetate in 70% acetic acid for 7 min [353]. Sebacoin (2-hydroxy-cyclodecanone) gives sebacil in 88-89% (equation 449) yield [359]. 

It is clear that the efficiency of the different stabilizers highly depends on the model system. PAOs are effective in all systems, but HAS are not effective in decalin. The oxidation of decalin mainly takes place at the tertiary carbon, leading to cyclodecanone and cyclodecanol [8]. This oxidation does not lead to the formation of aldehydes and acids. When aldehydes are added to decalin HAS becomes effective, so HAS is effective against the oxidation of aldehydes. HAS is also effective against the oxidation of squalane, which, like decalin, is a hydrocarbon containing secondary and tertiary carbons. However, because of its... 

Figure 1. Diagrammatic representation of olfactory receptor cell activity during odour stimulation. The spot size is roughly proportional to spike frequency (spike/min). Receptor cells taken at random from the epithelium of a frog are identified hy a serial number in the left column (60 in all). ACE - acetophenone, ANI - anisole, BUT - n-butanol, CAM - DL-camphor, CDN - cyclodecanone, CIN - cineole, CYM, p-cymene, DCT D-citronellol, HEP - n-heptanol, ISO - isoamylacetate, IVA - isovaleric acid, LIM -D-linonene, MAC - methyl-amylketone, MEN - L-menthol, PHE - phenol, PHO -thiophenol, PYR - pyridine, THY - thymol, XOL - cyclohexanol, XON - cyclohexanone. (From Sicard Holley [7]).

I 14. Oxidation of cyclodecanol to cyclodecanone is rapid with Cr03 in acid but reduction of cyclodecanone to... 

Zinc is the classical reagent for removing a ketone carbonyl via reaction with zinc amalgam (Zn/Hg) in HCl, the Clemmensen reduction. lO Reduction of ketone 534 to 535 is an example of this conversion. The effectiveness of using zinc in acid for reduction is seen in the removal of a hydroxyl group from an acyloin such as 536 (sec. 13.8.E) to give cyclodecanone, 537.5 2 a useful modification of this reaction was... 

When treated with HI in refluxing acetic acid, a-diketones and a-ketols are reduced to satd. ketones. This provides a general ketone synthesis, which in certain cases may be used to shift a carbonyl group to an adjacent position.— E Crude sebacil or sebacoin dissolved in glacial acetic acid, and refluxed 2-2.5 hrs. with 47% HI cyclodecanone. Y 80% from sebacil, 70% from sebacoin. F. e. s. W. Reusch and R. LeMahieu, Am. Soc. 86, 3068 (1964) cf. Steroids 5, 109 (1965). 

C-1. The product distribution was found to depend upon the amount of water present in the system, more 6-(bromomethylene)cyclodecanone being obtained with less water present. This observation was explained in terms of capture of the carbonium ion formed from (56 = 2). There would seem to be no examples yet where an intramolecular shift process competes with ring-opening of a cyclopropyl cation. Solvolysis of 10,10-dibromo[4,3,l]propellane in acetic acid-sodium acetate-acetic anhydride gave products formed via the strained bicyclic acetate (56 n = 1, R = Ac). In the absence of acetic anhydride products derived from the corresponding alcohol (56 n = 1, R — H) were obtained as well. Solvolyses of 10,10-dibromo[4,3,l]propell-3-ene in acetic acid-sodium acetate, in the presence and absence of acetic anhydride, and in acetic acid-silver perchlorate, were also reported. Most of the products may have been formed by reaction pathways similar to those observed for (55). ... 

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