《Further Investigation on the Rearrangement Mechanism of Reactions of 1,5-Benzothiazepines with Ethoxycarbonylcarbene》.pdfVIP

CHEM. RES. CHINESE U. 2006 ，22 （1 ），36—39 Further Investigation on the Rearrangement Mechanism of Reactions of 1 ，5-Benzothiazepines with Ethoxycarbonylcarbene ! WU Chun-zan ，HUANG Jia-xing ，ZHANG Oi-han and XU Jia-xi !! Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education ， College of Chemistry and Molecular Engineering ，Peking UniUersity ，Beijing 100871，P. R. China Received May 11 ，2005 The reactions of 2 ，3-dihydro-1 ，5-benzothiazepines with ethoxycarbonyicarbene undergo compiex rearrangements to produce ring-opening and ring contraction products. Previousiy it was presumed that the different products were formed Uia different mechanisms depending on the kind of substituents at the 2-position of 1 ，5-benzothiazepines. However ，on the basis of the further detaiied investigation ，it was found that aii 1 ，5-benzothiazepines can undergo the same rearrangement to yieid both ring-opening and ring contraction products. Keywords 1 ，5-Benzothiazepine ；Ethoxycarbonyicarbene ；Rearrangement ；Ring-contraction ；Ring-opening Article ID 1005-9040 （2006 ） -01-036-04 Introduction arrangements in the reactions of 2 ，3-dihydro-1 ，5- During the iast decade ，our group has investigated benzothiazepines with ethoxycarbonyicarbene ，and pro- a series of cycioaddition reactions of 2 ，3-dihydro-1 ，5- posed a possibie mechanism firstiy in 1991. Later Jin benzothiazepines with !-carbonyi-ketenes［1，2 ］，nitriie and co-workers studied this r