PREPARATION AND DIELS-ALDER REACTIONS OF 1,1-DICARBONYLALKENES
PREPARATION AND DIELS-ALDER REACTIONS OF 1,1-DICARBONYLALKENES
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DOI：
10.1021/jo00142a028
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发表时间：
1982-01-01
影响因子：
3.6
通讯作者：
MAGEE, AS
中科院分区：
文献类型：
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作者：
HOYE, TR;CARUSO, AJ;MAGEE, AS
1,1 -二羰基（酯、酮、内酯）取代烯烃由相应的饱和1-苯基磺酰基衍生物制备。它们是由前体硫化物形成的，可以通过氧化/ s -羟基-a-苯基亚砜羰基化合物或用酸性氯化物直接酰基化苯基亚砜烯酸盐阴离子来有效地制备。有些标题化合物可以分离出来然后反应，而另一些则生成并以Diels-Alder方式与环戊二烯原位反应。讨论了内-外选择性。本实验室目前正在研究亲二氧基-碳甲氧基-1-酮烯的分子内Diels-Alder化学。在此基础上，研究了这些亲二酚类化合物及其前体亚砜的制备方法，并对这些化合物的一些分子间diel - alder反应进行了研究。这里描述了这些观察结果。
1, 1-Dicarbonyl-(ester, ketone, lactone) substituted alkenes are prepared from the corresponding saturated 1-phenylsulfmyl derivatives. These are formed from precursor sulfides, which can be efficiently prepared either by oxidation of/S-hydroxy-a-phenylsulfenylcarbonyl compounds or direct acylation of-phenylsulfenyl enolate anions with acid chlorides. Some of the title compounds can be isolated and then reacted while others are generated and reacted insitu in a Diels-Alder fashion with cyclopentadiene. Endo-exo selectivities are discussed.In a current study in our laboratory the intramolecular Diels-Alder chemistry of dienophilic1-carbomethoxy-1-ketoalkenes is being investigated. In connection with this work, methods for the preparation of these dienophiles and their precursor sulfoxides1 have been developed, and some intermolecular Diels-Alder reactions2 of the title com-pounds have been examined. Those observations are de-scribed here.