The stereochemistry of β-chlorovinyl-aldehydes

Gagan, J. M. F.; Lane, Allen G.; Lloyd, Douglas R.

doi:10.1039/j39700002484

Cited by 30 publications

(16 citation statements)

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“…The starting aldehydes were synthesized from the corresponding ketones using the Vilsmeier-Scheme 1 TABLE 1 Synthesis of N-Acylhydrazones 1-6 1 2 [24] 3 [25] 4 [26] 5 [27] 6 [27] Haack reaction according to literature procedures [24][25][26][27]. The 4-tert-butylphenoxyacetylhydrazide used was also obtained as described in the literature [28].…”

Section: Synthesis Of N-acylhydrazones 1-6mentioning

confidence: 99%

Synthesis, Characterization, and Conformational Study of Acylhydrazones of α,β‐Unsaturated Aldehydes

Hamzi

Barhoumi‐Slimi²,

Abidi

2016

Heteroatom Chemistry

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Section: Synthesis Of N-acylhydrazones 1-6mentioning

confidence: 99%

Synthesis, Characterization, and Conformational Study of Acylhydrazones of α,β‐Unsaturated Aldehydes

Hamzi

Barhoumi‐Slimi²,

Abidi

2016

Heteroatom Chemistry

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“…The 31 P NMR spectrum of each of the phosphates 3 shows, as expected, two unequal intensity signals indicating the presence of the two Z and E isomers in different proportions. The integration of these signals gave approximately the same isomer percentages as those observed in the starting aldehydes 1 [27][28][29] and alcohols 2 [30].…”

Section: Spectroscopic Characterizationmentioning

confidence: 68%

“…The integration of these signals gave approximately the same isomer percentages as those observed in the starting aldehydes 1 [27][28][29] and alcohols 2 [30].…”

Section: Spectroscopic Characterizationmentioning

confidence: 96%

“…These were carefully measured from our own samples that were consistent with literature values [27][28][29] and compared with those obtained for phosphates 3 ( Table 2).…”

Section: Figurementioning

confidence: 98%

“…Our strategy to prepare the new allylic phosphates (Scheme 1) is based on the use of the starting β−chloro-α,β-unsaturated aldehydes 1, prepared by the Vilsmeier-Haack reaction [27][28][29], which were reduced using NaBH 4 in THF as previously described [30] to give the corresponding allylic alcohols 2. These were reacted with a phosphorochloridate to yield allylic phosphates 3.…”

Section: Synthesismentioning

confidence: 99%

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Synthesis and Characterization of New Variously Substituted Allylic Phosphates

Bahri

Barhoumi‐Slimi

Sanhoury

et al. 2016

Heteroatom Chemistry

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The Vilsmeier Reaction of Non‐Aromatic Compounds

Jones

Stanforth

2000

Organic Reactions

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This chapter extends the discussion to reactions between the Vilsmeier‐Haack reagent (subsequently referred to as the Vilsmeier reagent for brevity) and any other compounds in which a carbon‐carbon bond is formed. The discussion thus excludes reactions in which the Vilsmeier reagent acts as a chlorinating agent (for example in the preparation of acid chlorides), or in which it forms carbon‐oxygen or carbon‐nitrogen bonds, unless these are accompanied by formation of a carbon‐carbon bond. For a discussion of the nature of the reagent and of the mechanism of the reaction, the earlier chapter in vol. 49 should be consulted. There are also a number of reviews that deal at length with mechanisms of reactions involving the Vilsmeier reagent, notably those by Jutz and Marson, and hence this chapter will concentrate on applications, with brief mention of mechanisms when necessary. Wizinger has pointed out that alkenes could react with the Vilsmeier reagent, but his only examples were styrenes where the intermediate carbocation has considerable stability. Hydrolysis gives the cinnamaldehyde. In principle, any alkene which is not too sterically hindered can undergo this reaction, but the Vilsmeier reagent has low reactivity as an electrophile, and in practice activation is often necessary. The addition depends on the HOMO of the alkene, and anything increasing the HOMO energy will aid reaction, as for example further conjugation (dienes, trienes, etc.) or the presence of an electron‐donating substituent. Hence aldehydes and ketones are active in their enol forms, and enol ethers and enamines are good substrates. Indeed, all additions covered by this chapter can be regarded as alkene additions, even those on active methyl groups attached to electron‐deficient rings. As with any reaction involving carbocation intermediates, rearrangements are possible; the initial products are sometimes enamines, and this can give rise to polysubstitution. The substrates are grouped into eleven major subsections; references to reviews of particular relevance will be found in the appropriate subsection.

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The stereochemistry of β-chlorovinyl-aldehydes

Cited by 30 publications

References 0 publications

Synthesis, Characterization, and Conformational Study of Acylhydrazones of α,β‐Unsaturated Aldehydes

Synthesis, Characterization, and Conformational Study of Acylhydrazones of α,β‐Unsaturated Aldehydes

Synthesis and Characterization of New Variously Substituted Allylic Phosphates

The Vilsmeier Reaction of Non‐Aromatic Compounds

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