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

doi:10.1039/DT9870001647

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 journal › Article › peer-review

6 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 C_ylide-P to P-C_ylide to C_ylide-P distances of 1.742(4), 1.700(5), and 1.726(5) Å; cf. P-C_Me ca. 1.8 and P-C_ylide 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 language	English
Pages (from-to)	1647-1653
Number of pages	7
Journal	Journal of the Chemical Society. Dalton Transactions
Issue number	7
DOIs	https://doi.org/10.1039/DT9870001647
Publication status	Published - Jul 1987
Externally published	Yes

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Engelhardt, L. M., Papasergio, R. I., Raston, C. L., Salem, G., Whitaker, C. R., & White, A. H. (1987). 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 . Journal of the Chemical Society. Dalton Transactions, (7), 1647-1653. https://doi.org/10.1039/DT9870001647

Engelhardt, Lutz M. ; Papasergio, Rocco I. ; Raston, Colin L. et al. / 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 . In: Journal of the Chemical Society. Dalton Transactions. 1987 ; No. 7. pp. 1647-1653.

@article{53905531f572498cba75677d2e095daa,

title = "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 ",

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 {\AA} deviation), with Cylide-P to P-Cylide to Cylide-P distances of 1.742(4), 1.700(5), and 1.726(5) {\AA}; cf. P-CMe ca. 1.8 and P-Cylide 1.69(1) {\AA} 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.",

author = "Engelhardt, {Lutz M.} and Papasergio, {Rocco I.} and Raston, {Colin L.} and Geoffrey Salem and Whitaker, {Claire R.} and White, {Allan H.}",

year = "1987",

month = jul,

doi = "10.1039/DT9870001647",

language = "English",

pages = "1647--1653",

journal = "Journal of the Chemical Society. Dalton Transactions",

issn = "1472-7773",

publisher = "Royal Society of Chemistry",

number = "7",

}

Engelhardt, LM, Papasergio, RI, Raston, CL, Salem, G, Whitaker, CR & White, AH 1987, '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 ', Journal of the Chemical Society. Dalton Transactions, no. 7, pp. 1647-1653. https://doi.org/10.1039/DT9870001647

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 . / Engelhardt, Lutz M.; Papasergio, Rocco I.; Raston, Colin L. et al.
In: Journal of the Chemical Society. Dalton Transactions, No. 7, 07.1987, p. 1647-1653.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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 ...

T2 - CHPMe2C(PMe3)C10H6 and of a distorted peri-ylide, 1-Me-8-(Me3PCH)C10H6

AU - Engelhardt, Lutz M.

AU - Papasergio, Rocco I.

AU - Raston, Colin L.

AU - Salem, Geoffrey

AU - Whitaker, Claire R.

AU - White, Allan H.

PY - 1987/7

Y1 - 1987/7

N2 - 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.

AB - 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.

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U2 - 10.1039/DT9870001647

DO - 10.1039/DT9870001647

M3 - Article

SN - 1472-7773

SP - 1647

EP - 1653

JO - Journal of the Chemical Society. Dalton Transactions

JF - Journal of the Chemical Society. Dalton Transactions

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ER -

Engelhardt LM, Papasergio RI, Raston CL, Salem G, Whitaker CR, White AH. 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 . Journal of the Chemical Society. Dalton Transactions. 1987 Jul;(7):1647-1653. doi: 10.1039/DT9870001647

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