DIAZO ALKANE ADDUCTS OF THIETE SULFONE (THIACYCLOBUTENE 1,1-DIOXIDE) IN SYNTHESIS OF THIABICYCLOPENTANE DIOXIDES, PYRAZOLES, AND TETRAHYDROTHIOPHENE SULFONES
DIAZO ALKANE ADDUCTS OF THIETE SULFONE (THIACYCLOBUTENE 1,1-DIOXIDE) IN SYNTHESIS OF THIABICYCLOPENTANE DIOXIDES, PYRAZOLES, AND TETRAHYDROTHIOPHENE SULFONES
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DOI：
10.1021/jo00829a030
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发表时间：
1970-01-01
影响因子：
3.6
通讯作者：
GLASSMAN, R
中科院分区：
文献类型：
--
作者：
DITTMER, DC;GLASSMAN, R
重氮烷被加到硫杂环丁烯砜（硫杂环丁烯1，1-二氧化物）的双键上，得到1-或2-吡唑啉。二苯基重氮甲烷或甲基苯基重氮甲烷的加合物在加热或紫外线照射下失去氮，得到2-硫代双环[2.1]。0]戊烷2，2-二氧化物。与此相反，苯基重氮甲烷和对甲氧基苯基重氮甲烷的加合物失去二氧化硫，得到吡唑。硫杂双环戊烷砜是由硫杂双环戊烷砜合成噻吩砜（四氢噻吩）的一种途径。噻吩砜具有活性双键，它和取代的噻吩砜在Diels-Alder反应中容易加成阴离子，是亲双烯体。重氮烷烃与非环状和环状的β，β-不饱和砜的1，3-环加成是已知的。重氮烷烃与硫杂环丁烷砜的加合物可能是合成高张力体系（如双环丁烷）中潜在有用的中间体，如果同时或
Diazoalkanes have been added to the double bond of thiete sulfone (thiacyclobutene 1, 1-dioxide) to yield 1-or 2-pyrazolines. Adducts of diphenyldiazomethane or methylphenyldiazomethane lose nitrogen on heating or on irradiation with ultraviolet light to give2-thiabieyclo [2.1. 0] pentane 2, 2-dioxides. In contrast, the adducts of phenyldiazomethane and p-methoxyphenyldiazomethane lose sulfur dioxide to give py razóles. A route to thiophane (tetrahydrothiophene) sulfones from the thiabicyclopentane sulfones is shown.Thiete sulfone has a reactive double bond; it and substituted thiete sulfones add anions readily and are dienophiles in the Diels-Alder reaction. 4 1, 3-Cycloadditions of diazo alkanes with acyclic63 and cyclic5b,/3-unsaturated sulfones are known. Adducts of diazo alkanes with thiete sulfone may be potentially useful intermediates in the synthesis of highly strained systems (such as bicyclobutanes) if thesimultaneous or