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1676 MARSTON TAYLOR BOGDRT AND CLARENCE PEAVU IIARRIS. By reducing a solution o f t he free radical with hydrogen a t a tern- perature o € about 100 ) and identifying the products formed, it was hoped that it would prove possible to determine whether such a dissociation o f the monomolecular diphenylnaphthylmethyl occurs . But as in th e c ase o f reduction at ordinary temperatures, the reduced solution contained only diphenylnaphthyl methane so far as the examination revealed. an d yet i t seems difficu lt t o fi nd any other explanatio n equally satisfactory. 5. Summary. (I) Several new d i p h e n yl a n ap h th yl m e t hyl derivatives have been synthesized and described. 2 ) Th e importa nt che mica l reactio ns o f the free radical, diphenyl-a- naphthylmethyl, have been studied including the oxidation, the reduction, the action o f iodin e, th e action o f l ight, and the action of hydrochloric acid. (3) I t has been shown that diphenyl-a-naphthylmethyl, unlike tri- phenylmethyl, does not form additive compounds with various solvents, in s pi te o f it s high degree o f dissociation, and a plausible explanation for this difference has been suggested. (4) By mea ns of a series o f exa ct molecula r-weig ht de te rmin at io ns of diphenyl-a-naphthylmethyl extending over a range of temperature from o to Soo, it has been proven that the temperature as well as the con- cen tra tio n has a marked influence upon t he degree o f dissociation of free radicals , while the nature of the solvent seems t o exert bu t slight in- fluence. (5) It has been shown that at a temperature of approximately 60' diphenyl-a-naphthylmethyl is present in the monomolecular phase en- tirely, and that above this temperature the molecular weight suffers a further decrease, the cause of which has not been established. ANN ARBOR, niIctI [CONTRIBUTION ROM THE CHEMICAL ABORATORIES F COLUMBIA NIVERSITY, No. 323.1 THE SYNTHESIS OF SOME HOMOLOGS OF THE TERPENES, DERIVATIVES OF I ,4-DIPSOPROPYL CYCLOHEXANE. BY MARSTON AYLOR OGERT ND CLARENCE EAVY HARRIS.' Received July 24, 1919. Introductory Part. A n interesting fact concerni ng the terpenes, and one to which attention often has been called, is that the graphic formulas conventionally assigned 1 The investigation reported in this article formed part o f t he work carried out by Mr. Harris as a candidate for the degree of Ph.D. under the Faculty o f Pure Science, Columbia University, It s publication has b een delayed by the war duties of the senior author.

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Page 1: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 2: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 3: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 4: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 5: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 6: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 7: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 8: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 9: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 10: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 11: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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Page 14: Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

8/10/2019 Journal of the American Chemical Society Volume 41 Issue 10 1919 [Doi 10.1021_ja02231a017] Bogert, Marston Taylor; Harris, Clarence Peavy

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