Synthese von 1-adamantyl-acetaldehyden and homoadamantan-4-onen aus acetylen

Bott, Kaspar

doi:10.1016/s0040-4039(01)88001-1

Cited by 13 publications

(8 citation statements)

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“…Analysis of the AA'XX' system gave the following coupling constants: J2,3 = J4,5 = 6.73 Hz, J3,4 = 6.18 Hz, On the basis of the coupling constants, the possibility that the complex possesses the cycloheptatriene structure (2b) seems to be ruled out. As can be seen from Table 1, (2) shows more similarity to (4) than t o (3) as regards the coupling of the olefinic protons. This is particularly true of the relative magnitudes of J2,3 and J3,4 and of J2,4 and J2.5.…”

Section: )mentioning

confidence: 84%

“…The complex, which is stable on exposure to air, was obtained in analytically pure form (sinters above 95 OC with decomposition) by sublimation (90 "C, 10-4 torr) and subsequent recrystallization from nhexane; yield 67% (based on (NH3),Cr(CO)3). Since (2) contains three CO groups, six electrons of the C~oHlz ligand must be involved in bonding with the chromium atom. This finding, together with the observation that ( 2 ) regenerates the starting hydrocarbon on treatment with 2,2'-diaminodiethylamine 151 restricts the possible structures to the two alternatives (2a) and (2b) given above.…”

Section: )mentioning

confidence: 99%

“…A clearer insight into the s-electron structure of (2) is provided by the 1H-NMR spectrum (in CsD6). Thus the four olefinic protons give rise to an AA'XX' system with 72,s = 4.29 and ~3 , 4 = 5.51, the two bridge protons to an AB systems with T = 10.82 and 12.43 (J = 3.4 Hz), and the six protons of the (CH2)3 bracket to a multiplet between z = 8.2 and 9.7.…”

Section: )mentioning

confidence: 99%

“…The question whether (2) may be regarded as homoaromatic should prove most readily answerable on the basis of the chemical shifts. As shown in Table 2, the transition of ( I ) into the tricarbonylchromium complex (2) carbonylchromium ( 4 ) in which the geometrical conditions should resemble those in the present system.…”

Section: )mentioning

confidence: 99%

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1‐tert‐Butylvinyl Trifluoromethanesulfonate: Solvolysis and Rearrangement via a Vinyl Cation

Martı́nez¹,

Hanack²,

Summerville³

et al. 1970

Angew. Chem. Int. Ed. Engl.

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Section: )mentioning

confidence: 84%

Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

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1‐tert‐Butylvinyl Trifluoromethanesulfonate: Solvolysis and Rearrangement via a Vinyl Cation

Martı́nez¹,

Hanack²,

Summerville³

et al. 1970

Angew. Chem. Int. Ed. Engl.

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“…An intramolecular ring closure of the resulting ketoaldehyde (23) followed by further reaction steps affords guaiazulene (24)["].…”

Section: Unsaturated Aldehydes By Hydroformylation Of Non-conjugated mentioning

confidence: 99%

Synthesis of Intermediates by Rhodium‐Catalyzed Hydroformylation

Siegel¹,

Himmele²

1980

Angew. Chem. Int. Ed. Engl.

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Intramolecular additions of carbocations to a C-C triple bond or to a chlorovinyl group provide a pathway to cycloalkanones and cycloalkyl ketones. Such syntheses proceeding via ring closure which have already been redo not generally require a strongly acidic medium but can instead be performed in formic acid or trifluoroethanol. ConclusionThe methods considered in this review for the synthesis of carboxylic acids, aldehydes, and ketones are not only of preparative importance but also permit a further insight into the chemical behavior of carbocations. Thus the first generation of a "primary" vinyl cation [(55a)] devoid of stabilizing substituents was accomplished by addition of the I-adamantyl cation to acetylene and the reaction of this cation monitored. On the other hand, it has been found that the reactions of amidomethyl cations with chloroolefins in sulfuric acid do not involve a carbocation but an oxazonium ion as intermediate. These results could prove valuable for the planning of new syntheses. The availability of the starting materials should also encourage the exploitation of these reactions. (1971). (1978). Synthesis of Intermediates by Rhodium-Catalyzed Hydroformylation By Hardo Siegel and Walter Himmele[']Dedicated to Professor Matthias Seefelder on the occasion of his 60th birthdayThe reaction of olefins with carbon monoxide and hydrogen to give aldehydes is referred to as hydroformylation (0x0 reaction). As catalyst for this reaction rhodium is about three to four orders of magnitude more active than the more commonly employed cobalt. With special rhodium compounds, e. g. di-p-chlorobis(q-l,5-cyclooctadiene)dirhodium [RhCl(CsH1z)]z, in the presence of chiral phosphanes, even asymmetric hydroformylations can be achieved; however, the enantiomeric purity of the products (20-30%) is not high enough for industrial-scale syntheses.

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Vinyl and Allenyl Cations

Stang

1973

Progress in Physical Organic Chemistry

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Synthese von 1-adamantyl-acetaldehyden and homoadamantan-4-onen aus acetylen

Cited by 13 publications

References 1 publication

1‐tert‐Butylvinyl Trifluoromethanesulfonate: Solvolysis and Rearrangement via a Vinyl Cation

1‐tert‐Butylvinyl Trifluoromethanesulfonate: Solvolysis and Rearrangement via a Vinyl Cation

Synthesis of Intermediates by Rhodium‐Catalyzed Hydroformylation

Vinyl and Allenyl Cations

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