Über die Addition von Halogenwasserstoff an Isopren

Staudinger, H.; Kreis, W.; Schilt, W.

doi:10.1002/hlca.19220050513

Cited by 34 publications

(15 citation statements)

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“…1 3 0 2~. 1278w, 1252s, 1211m, 1168m, 1115s, 1027m, lOIOs, 925w, 895w 29803, 2945s, 2885m, 2855w, 2840w, 1775w, 1700m, l664w, 1610~1, 1588w, 1470s, 1457s, 14133, 1378w, 1348rn, 1330~1, 1297m, 1261?n, 1219w, 1204m, 1161s, 1218s, 1095w, 1079w, 1069w, 1030s, 1018s, 984m, 951x1, 936w, 850w [31] 10 g 3,3-Dimethylallylbromid [32] innerhalb von 10 Min. zugetropft.…”

Section: Lithiierung Und Reaktionen Mitmentioning

confidence: 99%

3,4‐Dimethoxyfuran: Eigenschaften, Berechnungen und Substitutionsreaktionen

Iten

Hofmann

Eugster

1978

Helvetica Chimica Acta

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In memoriam Prof. H. Lubhart(1 1 .x1.77) 3,4-Dimethoxyfuran: Properties, Calculations and some Substitution Reactions Summary 3,4-D6methoxyfuran (3,4-DF) is much more reactive than furan itself. We present experimental details €or the synthesis of this useful compound in 50-100 g batches. 3,4-Dibenzyloxyfuran has also been prepared. Quantum mechanical calculations by PPP-and CNDO-methods analogous to furan itself gave the following inforimation (compared with furan): enhanced negative partial charge at C (2) and c(5), higher acidity at a-positions, a stronger and at the same time inverted dipol moment. In accordance with the calculations, 3,4-DF can easily be substituted by weak electrophilic reagents, e.g. in a typical Mannich reaction. The bis-amino compound 8 is produced in good yields. Lithiation by butyl-Li leads to mono-or di-substituted products. The mono-and di-Li-3,CDF have been used for the preparation of various acylated and alkylated 3,4-DF derivatives.By acid hydrolysis of 3,4-DF crystalline 4-methoxy-3 (2 H)-furanone has been prepared.3,4-Diimethoxyfuran ( = 3,4-DF) wurde von uns gelegentlich zu Reaktionen mit Chinonen und anderen Dienophilen benutzt [3-91. Die dabei zu Tage getretene, gegenuber Furan deutlich erhohte Reaktivitat veranlasste uns, die chemischen und physikalischen Eigenschaften naher zu untersuchen, woruber in dieser und in spateren Arbeiten berichtet werden s0113).

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Section: Lithiierung Und Reaktionen Mitmentioning

confidence: 99%

3,4‐Dimethoxyfuran: Eigenschaften, Berechnungen und Substitutionsreaktionen

Iten

Hofmann

Eugster

1978

Helvetica Chimica Acta

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“…Interestingly, in the case cited the abnormal rearrangement product leads to the natural product anisoxide. 21 Base-catalyzed rearrangements of quaternary ammonium salts, derived from the reaction of tertiary amines with allylic halides (such as 1-bromo-3-methyl-2-butene), generally proceed via a [3,2]-sigmatropic rearrangement in aprotic solvents (eq 12). There is, however, often a competing 1,2-Stevens rearrangement.…”

mentioning

confidence: 99%

1-Bromo-3-methyl-2-butene

Gammill

2001

Encyclopedia of Reagents for Organic Synthesis

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“…Необходимо отметить, что пренилмалоновый эфир не во всех опытах выделялся в чистом виде, а в некоторых случаях его содержание в продуктах определялось методом газо-жидкостной хроматографии. Для идентификации пика пренилмалонового эфира применялся образец, синтезированный известным способом из изопрена [ 9 ].…”

unclassified

“…Чтобы дополнительно доказать строение полученного нами пренилмалонового эфира, он был превращен посредством омыления в пренилмалоновую кислоту (температура плавления последнего соответствовала указанной в литературе) и затем декарбоксилированием в пренилуксусную кислоту [ 9 ].…”

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