The fate of the isobutyldiazonium ion

Bayless, John H.; Jurewicz, Anthony T.; Friedman, Lester

doi:10.1021/ja01018a054

Cited by 7 publications

(4 citation statements)

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“…migration in the homoallylic cation is at least slower than solvent capture, whereas significant methyl migration occurs in the acetolysis of isobutyldiazonium cation. 19 This discrepancy may relate to partial stabilization of the primary cation center by the proximate double bond.…”

Section: Discussionmentioning

confidence: 99%

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Catalytic and photolytic decomposition of 1-chloro-4-diazoalkenes

Atkins¹,

Trost²

1972

J. Org. Chem.

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A solution of 11.8 mg (0.054 mmol) of 22 in ethyl acetate was hydrogenated in the presence of 10% Pd/C and the product was treated with HC1 in isopropyl alcohol to give 11.2 mg (81%) of irans-2-Ar-ethylamino-2-phenylcyclohexanol (23) hydrochloride,12 mp 207-209°, identical with an authentic sample.2-(l-Hydroxycyclopentyl)-2-phenyloxazolidine (24).-Treatment of 15.0 g (59.3 mmol) of bromo ketone 18 with 100 ml of 2aminoethanol as in the preparation of S gave 11.5 g (83.6%) of 24 after recrystallization from hexane: mp 94-95°; ir (KBr) 3475 cm-1 (OH); ir (CHCls) 1650 cm-1 (weak, C=N); uv £1, 208 nm (log e 3.80).

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Section: Discussionmentioning

confidence: 99%

“…Chem. Soc., 90, 2452(1968. Compound 6 exhibited the expected carbamate ir absorption at 3450, 3400, and 1705 cm-1.…”

mentioning

confidence: 90%

Catalytic and photolytic decomposition of 1-chloro-4-diazoalkenes

Atkins¹,

Trost²

1972

J. Org. Chem.

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“…148 The deamination of 2-amino-2-hydroxy-(95) and 2-amino-1,3-dihydroxy-adamantanes ( 96) is accompanied by a carbon skeleton rearrangement leading to the formation of tricyclic ketones 97 and 98. 151 Hydroxyadamantanes are also synthesised from the corresponding nitrates, which, as was mentioned above, are prepared by the treatment of adamantanes with nitric acid. 21 Later, the reactions of substituted adamantanes with nitric acid in acetic anhydride was studied.…”

Section: Synthesis Of Hydroxyadamantanes and Their Nitratesmentioning

confidence: 99%

Reactions of adamantanes in electrophilic media

Моисеев¹,

Макарова²,

Земцова³

1999

Russ. Chem. Rev.

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“…A careful measurement of the splittings in the signals due to H-6', while the residual broadening due to interaction with H-10 was removed by decoupling, showed Je'.iob = 1-88 ± 0.03 Hz in la and 1.69 ± 0.03 Hz in lb, the largest homobenzylic interactions reported so far. [2][3][4][5][6] The assignment is confirmed by the spectrum of 5-methyl-7,8,9-trimethoxy-4a,10b-irans-l,2,3,4,4a,5,6,10b-octahydrophenanthridine-4a-d, in which the signal of H-6' has the same multiplicity as seen with the undeuterated la.…”

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confidence: 94%

New reaction of trithioorthoacetates. Reaction with acylating reagents

Hojo¹,

Masuda²

1975

J. Org. Chem.

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by preparing and chromatographing samples of the dinitrophenylhydrazones. Fractional crystallization of the crude mixture of 2,4-dinitrophenylhydrazones from ethanol gave a sample (mp 131-132°) which did not depress the melting point of a known sample of cyclopropylacetaldehyde 2,4-dinitrophenylhydrazone.Cyclopropyloxirane (3). Cyclopropanecarboxaldehyde, 7.0 g (0.10 mol), was stirred under nitrogen with 28.6 g (0.14 mol) of trimethylsulfonium iodide in 60 ml of dimethyl sulfoxide. A solution of 14.0 g of potassium iert-butoxide in 150 ml of dimethyl sulfoxide was added dropwise with stirring during 30 min while cooling. After stirring for an additional 15 min, 300 ml of water was added slowly while cooling with ice. The solution was extracted with ether (3 X 500 ml) and the extract was washed with water and dried over molecular sieves. Distillation on a Teflon spinning band column gave, after removal of ether and tertbutyl alcohol, 2.6 g of 3: bp 85-90°(lit.12b bp 100°); NMR (neat) 5 0.1-0.4 (m, 4 H, cyclopropyl CHa), 0.5-0.8 (m, 1 H, cyclopropyl CH), 2.4-2.7 (m, 2 H, ox-

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The fate of the isobutyldiazonium ion

Cited by 7 publications

References 1 publication

Catalytic and photolytic decomposition of 1-chloro-4-diazoalkenes

Catalytic and photolytic decomposition of 1-chloro-4-diazoalkenes

Reactions of adamantanes in electrophilic media

New reaction of trithioorthoacetates. Reaction with acylating reagents

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