Journal article
Bifunctional conjunctive reagents: 5-chloro-2-lithio-1-pentene and related substances. A methylenecyclohexane annulation method
Canadian journal of chemistry, v 71(3), pp 280-286
01 Mar 1993
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Abstract
The development of a new, synthetically useful methylenecyclohexane annulation method is described. Transmetallation (MeLi, tetrahydrofuran, −78 °C) of 5-chloro-2-trimethylstannyl-1-pentene (8) affords the novel bifunctional reagent 5-chloro-2-lithio-1-pentene (9), which, at temperatures higher than approximately −50 °C, self-destructs to give methylenecyclobutane (14). Reagent 9 can be converted into the Grignard reagent 10 and the organocopper(I) species 15. Conjugate addition of 10 and 15 to a number of cyclic enones (16–22), followed by intramolecular alkylation of the resultant adducts (23–29), produces the corresponding methylenecyclohexane annulation products (30–40).
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Details
- Title
- Bifunctional conjunctive reagents: 5-chloro-2-lithio-1-pentene and related substances. A methylenecyclohexane annulation method
- Creators
- Edward PiersBik Wah Anissa YeungFraser F. Fleming
- Publication Details
- Canadian journal of chemistry, v 71(3), pp 280-286
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:A1993KU98200002
- Other Identifier
- 991020898498004721
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- Web of Science research areas
- Chemistry, Multidisciplinary