Adelaide Research & Scholarship
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https://hdl.handle.net/2440/86808
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| Type: | Journal article |
| Title: | The synthesis of aza[n]ladderanes and azahomo[n]ladderanes containing β-lactams at the terminus |
| Other Titles: | The synthesis of aza[n]ladderanes and azahomo[n]ladderanes containing beta-lactams at the terminus |
| Author: | Warrener, R.N. Russell, R.A. Margetic, D. |
| Citation: | Synlett: accounts and rapid communications in synthetic organic chemistry, 1997; 1997(1):38-40 |
| Publisher: | Thieme Medical |
| Issue Date: | 1997 |
| ISSN: | 0936-5214 1437-2096 |
| Statement of Responsibility: | Ronald N. Warrener, Richard A. Russell, Davor Margetic |
| Abstract: | 5-Azabicyclo[2.2.0]hex-2-en-6-one 1 undergoes [2π+2π] cycloaddition with dimethyl acetylene dicarboxylate (Ru-catalysed) to yield aza[3]ladderane 2 which is transformed to aza[5]ladderanes 4 and 5 on treatment with cyclobutadiene and to azahomo[5]ladderanes 10 and 11 on reaction with cyclopentadiene. The specifities of these cycloaddition reactions are in agreement with predictions made using ab initio calculations. Chlorosulfonylisocyanate addition is used to access azahomo[4]ladderane 14. |
| Keywords: | cycloaddition-specifities polycyclobutanes chlorosulfonyl isocyanate ab initio calculations 5-azabicyclo[2.2.0]hex-2-en-6-one |
| Rights: | © Georg Thieme Verlag |
| DOI: | 10.1055/s-1997-697 |
| Published version: | http://dx.doi.org/10.1055/s-1997-697 |
| Appears in Collections: | Aurora harvest 2 Chemistry publications |
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