Cycloaddition reactions of indenes. 3. 1: 1 Adduct from 1,1-dimethyl-1H-indene and dimethyl acetylenedicarboxylate

Wayland E. Noland, Venkataraman Kameswaran

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

In contrast to 1H-indene (1a) and 1-methyl-1H-indene (1b), which give stable 1:2 adducts (3a, 34%; 3b, 30%) and with 1a also a 1:3 adduct (4a; 40% from 1a; 71% from 3a) with dimethyl acetylenedicarboxylate (DMAD), 1,1-dimethyl-1H-indene (1d) and DMAD gave as the only crystalline product a cycloadduct of different structural type, dimethyl 1a,7b-cis-dihydro-1,1-dimethyl-1H-cyclopropa[a]naphthalene-2,3-dicarboxylate (5a, 14%), the structure of which has been confirmed by X-ray crystallography.

Original languageEnglish (US)
Pages (from-to)1318-1322
Number of pages5
JournalJournal of Organic Chemistry
Volume46
Issue number7
StatePublished - 1981

Fingerprint Dive into the research topics of 'Cycloaddition reactions of indenes. 3. 1: 1 Adduct from 1,1-dimethyl-1H-indene and dimethyl acetylenedicarboxylate'. Together they form a unique fingerprint.

Cite this