Infrared Absorption Spectra of Some Cyclopropane and Cyclobutane Hydrocarbons

Derfer, John M.; Pickett, E. E.; Boord, Cecil E.

doi:10.1021/ja01175a071

Cited by 53 publications

(19 citation statements)

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“…The ability of the material in this fraction to replace biotin to a limited extent in the nutrition of L. arabinosus does suggest the presence of something other than palmitic acid since such straight-chain saturated fatty acids alone have no biotin replacing ability for lactic acid bacteria (Williams et al, 1947). Infrared studies of this material were not conclusive but did indicate a small absorption at 9.9 ,u which is observed to a more marked degree in compounds known to contain a cyclopropane ring (Derfer et al, 1949). A saturated C17 compound, if present, would be expected to appear in this fraction.…”

Section: Discussionmentioning

confidence: 75%

Involvement of Methionine in Bacterial Lipid Synthesis

O’Leary

1959

J Bacteriol

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Section: Discussionmentioning

confidence: 75%

Involvement of Methionine in Bacterial Lipid Synthesis

O’Leary

1959

J Bacteriol

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“…A cyclopropane ring was inferred from is bands at 3.25 and 9.80 pm (12 bWetermined by decoupling, except uhere otherwise indicated.…”

Section: Identity Of Plzotoproductmentioning

confidence: 99%

Photoisomerization of 1-triphenylmethylcyclopentadiene. Di-π-methane rearrangement to 5,6,6-triphenylbicyclo[3.1.0]hex-2-ene

Weigl¹,

Warkentin²

1977

Can. J. Chem.

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Triphenylmethylcyclopentadiene exists as a mixture of isomers, the minor and major components of which are shown to be 1-triphenylmethylcyclopentadiene (1) and 2-triphenylmethyl-cyclopentadiene (2), respectively.Direct irradiation of a mixture of 1 and 2 led to formation of 5,6,6,-triphenylbicyclo[3.1.0]hex-2-ene (3) via rearrangement of 1. Acetophenone-sensitized irradiation of the same mixture gave 3 as well as a two component mixture of photodimers of 1 and/or 2. Results are interpreted in terms of the di-π-methane rearrangement mechanism.

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“…This hydrocarbon was obtained from l-ethoxy-3-bromohexane by the procedure described for the preparation of ethylcyclopropane, except that ether was used in place of tetrahydrofuran, and dry toluene was substituted for xylene. All the material boiling up t o 111" was distilled from the reaction flask, and this distillate was re- The infrared absorption spectrogram of this product showed the 9.8-9.9 p band characteristic of the cyclopropane ring (9). Its identity was also verified by an independent synthesis of n-butylcyclopropane and comparison of the spectra of the two samples.…”

mentioning

confidence: 91%

CYCLOPROPANE HYDROCARBONS FROM gamma-BROMOETHERS¹

Gragson¹,

Greenlee²,

Derfer³

et al. 1955

J. Org. Chem.

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The synthesis of olefins by the de-alkoxybromination of beta-bromoethers with zinc in aqueous ethanol is a well known and highly developed reaction (1). Adaptation of the method to the preparation of cyclopropane hydrocarbons by the de-alkoxybromination from gamma-bromoethers has barely been tried.Wolkoff and Menschutkin (2) treated 1-ethoxy-3-bromopropane (ethyl ybromopropyl ether) with zinc dust in 96 % alcohol, and upon warming the reaction mixture to 60-70' obtained an '(almost theoretical yield" of propylene. Paul (3) treated 1-phenoxy-3-iodopropane with magnesium in dry butyl ether and obtained an ('abondant degagement" (copious evolution) of cyclopropane. He also attempted to prepare cyclopropane from 1-ethoxy-3-chloropropane by this method, but obtained none; reaction conditions were not specified. Hammonet (4) prepared Grignard reagents from many of the higher bromoethers, but made no attempt to convert them into the corresponding hydrocarbons.It may be said that, in general, far less work has been reported on methods of synthesis for mono-alkylcyclopropanes than for polyalkylcyclopropanes. In the course of the present research we have developed what appears to be a general method for the preparation of mono-alkylcyclopropanes by the de-alkoxybromination of ybromoethers with magnesium; the scheme of synthesis starts with the commercially available 3-ethoxypropionaldehyde (see equations 1-111). It was also found that cyclopropane, itself, and polyalkylcyclopropanes can be prepared in three steps (equations IV-VI) from appropriate homologs of trimethylene glycol.In the preparation of the mono-alkylcyclopropanes, 3-ethoxypropionaldehyde was condensed with a Grignard reagent to produce a y-hydroxyether, from which the corresponding ybromoether was prepared by reaction with phosphorus tribromide. I CzHsOCHzCHzCHO + RMgX + CzHsOCHzCH2CH(OH)R I1 3CzHsOCHzCH2CH(OH)R + PBrs -+ 3C2HsOCH2CHzCH(Br)R Br 1

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Infrared Absorption Spectra of Some Cyclopropane and Cyclobutane Hydrocarbons

Abstract: A F 13200 -33.6Tcal./mole AH = 13200 cal./mole A S = 33.6 cal./mole-deg.

Cited by 53 publications

References 0 publications

Involvement of Methionine in Bacterial Lipid Synthesis

Involvement of Methionine in Bacterial Lipid Synthesis

Photoisomerization of 1-triphenylmethylcyclopentadiene. Di-π-methane rearrangement to 5,6,6-triphenylbicyclo[3.1.0]hex-2-ene

CYCLOPROPANE HYDROCARBONS FROM gamma-BROMOETHERS¹

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Infrared Absorption Spectra of Some Cyclopropane and Cyclobutane Hydrocarbons

Abstract: A F 13200 -33.6Tcal./mole AH = 13200 cal./mole A S = 33.6 cal./mole-deg.

Cited by 53 publications

References 0 publications

Involvement of Methionine in Bacterial Lipid Synthesis

Involvement of Methionine in Bacterial Lipid Synthesis

Photoisomerization of 1-triphenylmethylcyclopentadiene. Di-π-methane rearrangement to 5,6,6-triphenylbicyclo[3.1.0]hex-2-ene

CYCLOPROPANE HYDROCARBONS FROM gamma-BROMOETHERS1

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CYCLOPROPANE HYDROCARBONS FROM gamma-BROMOETHERS¹