1988
DOI: 10.1002/chin.198842108
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ChemInform Abstract: 2‐Phenylsulfinylmethyl‐1,3‐butadiene in the Thermal Diels‐Alder Reaction.

Abstract: The phenylsulfinylbutadiene (Ia) is coupled with the dienophiles (II), (IV), or (IX) to give the Diels‐Alder products (IIIa), (V), or (X) and (XI).

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“…Readily available racemic 2-(phenylsulfinylmethyl)buta-1,3diene ( 405) is an active diene. 363 This compound reacted with dimethylcyclopropene to give a mixture of exo-and endo-adducts 406. After reductive desulfinylation, the exo-adduct was converted into D 3 -carene (407).…”
Section: B Sulfonyl-and Sulfinyl-containing Dienesmentioning
confidence: 99%
“…Readily available racemic 2-(phenylsulfinylmethyl)buta-1,3diene ( 405) is an active diene. 363 This compound reacted with dimethylcyclopropene to give a mixture of exo-and endo-adducts 406. After reductive desulfinylation, the exo-adduct was converted into D 3 -carene (407).…”
Section: B Sulfonyl-and Sulfinyl-containing Dienesmentioning
confidence: 99%
“…40 The rearrangements of the adducts of 2-phenylsulfinylbuta-1,3diene with 3,3-dimethylcyclopropene or methyl vinyl ketone afforded carenols 31 (a mixture of the a-and b-isomers in a ratio of 7.5 : 1) and a mixture of isomers of 4-acetyl-2-hydroxycyclohexanone (32), respectively. 41 The asymmetric tandem process consisting of the Diels ± Alder reaction and the sulfoxide ± sulfenate rearrangement can be performed with the use of enantiomerically pure 1-arylsulfinylbuta-1,3-dienes containing an electron-withdrawing substituent at position 4. Thus one-pot thermal reactions of such dienes with an excess of N-methylmaleimide gave rise to enantiomerically pure cyclohexene-containing compounds in high yields.…”
Section: + Brmentioning
confidence: 99%