Reductions with Dialkylaluminum Hydrides

Miller, Alfred E. G.; Biss, Jean W.; Schwartzman, Louis H.

doi:10.1021/jo01087a013

Cited by 115 publications

(29 citation statements)

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“…Commercially available alkyl aldehydes are converted in a standard Wittig-Horner reaction [48] to the trans acrylates. Reduction of these trans acrylates with diisobutylaluminium hydride [49] yielded the corresponding (E)-Zalkenyl-1-ols, which were used in a Mitsunobu reaction [SO] with the known 5-heptyl-, octyl-, and nonyl-2- …”

Section: Synthesismentioning

confidence: 99%

2-[4-Alkenyloxy)phenyl]-5-alkylpyrimidines The relationship between position and nature (E/Z) of the double bond and transition temperatures

Kelly

1993

Liquid Crystals

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To cite this article: S. M. Kelly (1993) 2-[4-Alkenyloxy)phenyl]-5-alkylpyrimidines The relationship between position and nature (E/Z) of the double bond and transition temperatures, Liquid Crystals, 14:3, 675-698,The 5-n-alkyl-2-[4-(n-alkoxy)phenyl]pyrimidines are essential components of most commercial chiral smectic C mixtures for eiectrooptic display devices based on ferroelectric effects. This is due to their generally relatively low melting points, enantiotropic, relatively wide range smectic C mesophases, low viscosity and ease of preparation. An unsaturated carbon-carbon double bond has now been introduced into the terminal alkoxy chain of the 5-n-alkyl-2-[4-(alkoxy)phenyl]pyrimidines to produce the corresponding alkenyloxy substituted derivatives. The position and nature ( E / Z ) of the double bond has been varied systematically and the effect on the liquid crystal transition temperatures studied. A number of homologous series of the most interesting alkenyloxy substituted materials has been prepared and evaluated. The position and nature ( E / Z ) of the double bond changes the conformation of the alkenyloxy chain substantially. This can result in significantly higher smectic C transition temperatures for compounds with a trans double bond (E) at an even number of carbon atoms from the molecular core. Significantly lower transition temperatures (including the melting point) are observed for materials with a cis double bond ( Z ) at an odd number of carbon atoms from the molecular core. Comparisons with the corresponding alkoxy substituted materials (i.e. without a double bond) are made.

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Section: Synthesismentioning

confidence: 99%

2-[4-Alkenyloxy)phenyl]-5-alkylpyrimidines The relationship between position and nature (E/Z) of the double bond and transition temperatures

Kelly

1993

Liquid Crystals

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“…The alcohol 11 was obtained by diisobutyl aluminium hydride reduction (12) of the ester 10 in 69% yield. The allylic chloride 12 prepared from 11 using Meyer's conditions (13) (yield: 86%) was treated with di-tert-butyl sodiomalonate to give the monosubstituted malonate 13 in 72% yield.…”

Section: Methodsmentioning

confidence: 99%

Transannular Diels–Alder cyclization of substituted 13-membered trienes. An approach to the B.C.D.[6.6.5] rings of the 14β-hydroxysteroids

Langlois¹,

Soucy²,

Dory³

et al. 1996

Can. J. Chem.

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Abstract:The transannular Diels-Alder strategy has been applied to three 13-membered macrocyclic trienes whose characteristics are: a cis-trans diene and a cis methoxymethyl en01 ether as the dienophile. The successful trials led to three 6.6.5 tricyles having a trans-syn-cis geometry exactly as in the B.C.D. rings of the 14P-hydroxysteroids.Key words: transannular, Diels-Alder, 14P-hydroxysteroids, 13-membered rings.Resum6 : La stratkgie de Diels-Alder transannulaire a CtC appliquke sur trois triknes macrocycliques B 15 membres dont les caractkristiques sont : un dikne cis-trans et un Cther d'Cnol rnCthoxymCthyle cis comme diknophile. Les essais positifs ont conduit ii trois tricycles 6.6.5 ayant une gComCtrie traizs-syn-cis exactement comme les cycles B.C.D. des 14P-hydroxystCro'ides.

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“…Preparation of I-Benzyl-4-piperidinols-l-Benzyl-4-piperidinols were prepared by the reduction of 1-benzyl-4-piperidones with diisobutyl aluminum hydride according to the method of Miller et al (4).…”

Section: Methodsmentioning

confidence: 99%