Prepackaged Ramberg–Bäcklund reagents: useful tools for organic synthesis
作者:Eric Block、Hak Rim Jeon、David Putman、Shao-Zhong Zhang
DOI:10.1016/j.tet.2004.06.032
日期:2004.8
synthesis and reactions of several α,β-unsaturated chloromethyl sulfones is presented, for example [(chloromethyl)sulfonyl]-1,3-propadiene (4), [(chloromethyl)sulfonyl]ethene (5), [(dichloromethyl)sulfonyl]ethene (6) and (E,Z)-1,2-bis[(chloromethyl)sulfonyl]ethene (7). These compounds serve as ‘prepackaged’ Ramberg–Bäcklund reagents, which following an appropriate first step, such as Diels–Alder addition
Goerdeler,J.; El Tom,I., Chemische Berichte, 1965, vol. 98, p. 1544 - 1555
作者:Goerdeler,J.、El Tom,I.
DOI:——
日期:——
Goerdeler,J. et al., Chemische Berichte, 1976, vol. 109, p. 3108 - 3114
作者:Goerdeler,J. et al.
DOI:——
日期:——
Chloromethanesulfonylethene and Dichloromethanesulfonylethene: New Reagents for Tandem Diels−Alder/Ramberg−Bäcklund Reactions
作者:Eric Block、Hak Rim Jeon、Shao-Zhong Zhang、Evgeny V. Dikarev
DOI:10.1021/ol0363523
日期:2004.2.1
Chloromethanesulfonylethene (3a) and dichloromethanesulfonylethene (3b) were prepared by oxidation of the adducts of ethylene and ClCH2SCl or Cl2CHSCl, respectively, followed by NaHCO3 dehydrochlorination. With dienes, 3a gave Diels-Alder adducts that, with base, underwent Ramberg-Backlund reaction, giving products corresponding to the adducts of the dienes and allene. Similarly, 3b gave Diels-Alder adducts that, with base in the presence of the novel chlorine source MeSO2CCl3, cleanly afforded products corresponding to the adducts of the dienes and 1,1-dichloropropa-1,2-diene.
Boberg et al., Justus Liebigs Annalen der Chemie, 1958, vol. 616, p. 1,17