Chemistry of 2,3-dihydro-2-metallaphenalenes. Part 2. Formation of [CHMMe2C(MMe3)C10H6]x via base decomposition of [1,8-(Me3MCH2)2C10H 6]y (M = Ge, x = 2-, y = 0; M = P, x = 0, y = 2+); crystal structures of the novel bis-ylide ... CHPMe2C(PMe3)C10H6 and of a distorted peri-ylide, 1-Me-8-(Me3PCH)C10H6

Lutz M. Engelhardt, Rocco I. Papasergio, Colin L. Raston, Geoffrey Salem, Claire R. Whitaker, Allan H. White

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Treatment of 1,8-(Me3GeCH2)2C10H6, derived from a Grignard in situ trapping reaction, with Li(Me2NCH2CH2NMe2)Bun in hexane yields the germanium heterocyclic dianion [CHGeMe2C(GeMe3)C10H6]2-, characterized as its protonolysis product. Potassium hydride and [1,8-(Me3PCH2)2C10H 6]Cl2 in tetrahydrofuran affords the novel bis-ylide HC=PMe2C(=PMe3)C10H6, (4), and small amounts of the mono-ylide 1-Me-8-(Me3P=CH)C10H6, (5). The ring system in (4) is planar, the heteroatom excepted (0.50 Å deviation), with Cylide-P to P-Cylide to Cylide-P distances of 1.742(4), 1.700(5), and 1.726(5) Å; cf. P-CMe ca. 1.8 and P-Cylide 1.69(1) Å in (5). The aromatic rings in (5) are twisted, the ylide carbon, which is almost 'co-planar' with the adjacent ring, and peri-methyl carbon being skewed in opposite directions.

Original languageEnglish
Pages (from-to)1647-1653
Number of pages7
JournalJournal of the Chemical Society, Dalton Transactions
Issue number7
DOIs
Publication statusPublished - Jul 1987
Externally publishedYes

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