Polar substituent effects on NMR chemical shifts of group 14 elements: Synthesis and NMR (13C, 29Si, 119Sn, and 207Pb) substituent chemical shifts (SCS) of 4-substituted bicyclo[2.2.2]oct-1-ylbutanes, -trimethylsilanes, -trimethylstannanes, and -trimethyl

W Adcock; H Gangodawila; G B Kok; V S Iyer; W Kitching; G M Drew; David James Young

doi:10.1021/om00144a029

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Polar substituent effects on NMR chemical shifts of group 14 elements: Synthesis and NMR (13C, 29Si, 119Sn, and 207Pb) substituent chemical shifts (SCS) of 4-substituted bicyclo[2.2.2]oct-1-ylbutanes, -trimethylsilanes, -trimethylstannanes, and -trimethyl

Journal article

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Polar substituent effects on NMR chemical shifts of group 14 elements: Synthesis and NMR (13C, 29Si, 119Sn, and 207Pb) substituent chemical shifts (SCS) of 4-substituted bicyclo[2.2.2]oct-1-ylbutanes, -trimethylsilanes, -trimethylstannanes, and -trimethyl

W Adcock, H Gangodawila, G B Kok, V S Iyer, W Kitching, G M Drew and David James Young

Organometallics, Vol.6(1), pp.156-166

1987

DOI: https://doi.org/10.1021/om00144a029

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Abstract

Full title: Polar substituent effects on NMR chemical shifts of group 14 elements: Synthesis and NMR (13C, 29Si, 119Sn, and 207Pb) substituent chemical shifts (SCS) of 4-substituted bicyclo[2.2.2]oct-1-ylbutanes, -trimethylsilanes, -trimethylstannanes, and -trimethylplumbanes (M(CH3)3, M = C, Si, Sn, and Pb) and 4-substituted bicyclo[2.2.1]hept-1-yltrimethylstannanes. An extensive series of 4-substituted bicyclo[2.2.2]oct-1-yltrimethylstannanes (2a) and 4-substituted bicyclo[2.2.1]hept-1-yltrimethylstannanes (3a) has been synthesized and characterized and the 119Sn chemical shifts measured. A remarkably wide range of substituent chemical shifts (SCS; ca. 20 ppm) are obtained for system 2a, and these have been analyzed in terms of possible substituent-probe interactions. Comparisons have been made between systems 2a and 3a, but the signs of the 119Sn substituent chemical shifts (SCS) for the two systems are diametrically opposed, indicating a different blend of "through-space" and "through-bond" effects. Some 4-substituted 1-tert-butylbicyclo[2.2.2]octanes (2b) as well as more restricted series of trimethylsilanes and trimethylplumbanes (2c and 2d, respectively) have also been acquired and their 13C, 29Si, and 207Pb SCS measured and compared with those of the stannane series. Synthetic approaches that provide efficient access to some 1,4-disubstituted bicyclo[2.2.2]octyl systems are outlined. © 1987 American Chemical Society.

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Title: Polar substituent effects on NMR chemical shifts of group 14 elements: Synthesis and NMR (13C, 29Si, 119Sn, and 207Pb) substituent chemical shifts (SCS) of 4-substituted bicyclo[2.2.2]oct-1-ylbutanes, -trimethylsilanes, -trimethylstannanes, and -trimethyl
Authors: W Adcock (Author)
H Gangodawila (Author)
G B Kok (Author)
V S Iyer (Author)
W Kitching (Author)
G M Drew (Author)
David James Young (Author)
Publication details: Organometallics, Vol.6(1), pp.156-166
Publisher: American Chemical Society
Date published: 1987
DOI: 10.1021/om00144a029
ISSN: 0276-7333
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449809402621
Output Type: Journal article

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