; Academic: New York,
1984; Vol. Macias, F. A.; Molinillo, J. M. G.;
Collado, I. G.; Massanet, G. M.; Rodriguez-Luis, F. TL
1990, 31, 3063. (c) Bailey, W. F.; Khanolkar, A. D. JOC
1990, 55, 6058. Acetaldehyde N-t-Butylimine;
Acetaldoxime; Crotonaldehyde;
Dimethylaluminum Chloride; Ethyl
Vinyl Ether; Formaldehyde; Formaldehyde-Dimethylamine;
Vinyl Acetate. 45.
(ii) Acetaldehyde is heated with aqueous sodium hydroxide solution
(iii) Formaldehyde reacts with sodium hydroxide. 16. # One of the most common ways to allow both acetaldehyde and acetone to react with Tollen’s reagent. Attacks copper, aluminum, zinc and their alloys. Thus when condensed with benzaldehyde, benzyl acetate is the
major product.34 Recently an
interesting and synthetically useful stereoselective intramolecular
Tishchenko reduction of b-hydroxy
ketones using acetaldehyde and promoted by Samarium(II)
Iodide, affording anti-1,3-diol monoacetates,
has been reported (eq 4).35 The
stereoselective pinacol cross-coupling of acetaldehyde with
other higher-order aldehydes that contain chelating functionalities
has been achieved using a vanadium(II) reagent.36
The photochemical addition of acetaldehyde in the presence
of molecular oxygen to a,b-unsaturated
esters and ketones provides excellent yields of the 1,4-dicarbonyl
compounds (eq 5).37
Pericyclic Reactions. Used to make other chemicals, vulcanize rubber. (a) Kent, R. E.; McElvain, S. M.
OSC 1955, 3, 591.
The thermal ene reactions of acetaldehyde and other aliphatic aldehydes with alkenes are generally not very productive.38 However, acetaldehyde can be induced to undergo ene reactions with a variety of alkenes under Lewis acid activation. Mikami, K.; Shimizu, M. CRV 1992, 92, 1021. 39. Clerici, A.; Porta, O. TL 1990, 31, 2069. B. JOC 1984, 49, 2443. Boldnini, G. P.; Mancini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. JCS(C) 1990, 1680.
which a carbon atom forms a solid bond with an (c) Doxsee, K. M.; Mouser, J. K. M. TL 1991, 32, 1687.
(b) Horning, E. C.; Denekas, M. O.; Field, R. E. OSC 1955, 3, 317. The mechanism for imine formation proceeds through the following steps: 1. (MW 44.05), (reagent used as two-carbon electrophilic component in a wide array of reactions). Boldnini, G. P.; Mancini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. JCS(C) 1990, 1680. RATINGS, REFRACTIVE 35. (d) Long, F. A.; Howard, J. W. OSC 1943, 2, 87. 30 The Pictet-Spengler reaction utilizing acetaldehyde is an important ring-forming reaction. INFORMATION, DESCRIPTION (a) Motoyoshiya, J.; Yazaki, T.; Hayashi, S. JOC 1991, 56, 735. 28. B. JOC 1984, 49, 2443.
Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed. 43. 21.
19.
14. Acetaldehyde, Kendall, E. C.; McKenzie, B. F. OSC 1932, 1, 21. Marshall, J. 45.
(a) Makin, S. M.; Él'yanov, B. S.; Raifel'd, Y. E. IZV 1974, 2654. IN WATER, VAPOR resins, and basic dyes. Thus when condensed with benzaldehyde, benzyl acetate is the major product.34 Recently an interesting and synthetically useful stereoselective intramolecular Tishchenko reduction of b-hydroxy ketones using acetaldehyde and promoted by Samarium(II) Iodide, affording anti-1,3-diol monoacetates, has been reported (eq 4).35 The stereoselective pinacol cross-coupling of acetaldehyde with other higher-order aldehydes that contain chelating functionalities has been achieved using a vanadium(II) reagent.36 The photochemical addition of acetaldehyde in the presence of molecular oxygen to a,b-unsaturated esters and ketones provides excellent yields of the 1,4-dicarbonyl compounds (eq 5).37 Pericyclic Reactions. (a) Amberg, W.; Seebach, D. CB 1990, 123, 2413.
Acetaldehyde reacts with a myriad of nucleophilic reagents ... whereby cyanide is added to the adduct of ammonia and acetaldehyde followed by hydrolysis of the intermediate a-aminonitrile. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed. Sugai, T.; Kakeya, H.; Ohta, H. JOC 1990, 55, 4643. Marshall, J.
37. 15. 21. The Drake, N. L.; Cooke, G. B. OSC 1943, 2, 407. 34. Allyl organometallics react with varying degrees of stereocontrol depending on the metal and conditions to give the corresponding homoallylic alcohols.8 Chiral allylboronates also react with acetaldehyde at -78 °C to afford the homoallylic alcohols with high enantioselectivity.9 trans-Epoxides are produced selectively through the Darzens reaction of acetaldehyde with halomethyl sulfones under basic phase transfer conditions.10 Classical Wittig reagents11 and Horner-Emmons phosphonate12 ylides react with acetaldehyde to give the alkene. Acetaldehyde can be generated from paraldehyde through acid catalyzed degradation of the trimer and isolated by distillation.43 The diethyl acetal of acetaldehyde, commonly known as acetal, may be generated from acetaldehyde or paraldehyde, ethanol, and calcium chloride.44 Acetaldehyde and paraldehyde have also been used for the protection of diols as their ethylidene acetals.45 Related Reagents. (a) Shiqi, P.; Min, G.; Winterfeldt, E. LA 1993, 137. The hetero-Diels-Alder reaction of acetaldehyde has been reported under high pressure acceleration with 1-alkoxydienes to afford good yields of dihydropyrans with modest endo selectivity.41 Paraldehyde and Other Acetaldehyde Derivatives. Adkins, H.; Nissen, B. H. OSC 1932, 1, 1. (e) Behforouz, M.; West, S. J.; Chakrabarty, C.; Rusk, D. A.; Zarrinmayeh, H. H 1992, 34, 483. Intramolecular Mannich reaction of acetaldehyde has been utilized to produce the natural product myrtine (eq 3).25 The intramolecular Mannich reaction has also been used in the synthesis of proline derivatives.26 Nucleophiles as diverse as dialkyl phosphites27 and amines28 or aryl radicals29 may also add to the intermediate imine of acetaldehyde in Mannich-type reactions.
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