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Journal of the American Chemical Society

Volumn 130, Issue 41, 2008, Pages 13549-13551

Thermal C1-C5 diradical cyclization of enediynes

(5) Vavilala, Chandrasekhar a Byrne, Neal b Kraml, Christina M b Ho, Douglas M c Pascal Jr , Robert A a

a PRINCETON UNIVERSITY (United States)

b LOTUS SEPARATIONS LLC (United States)

c HARVARD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENEDIYNE; ALKADIENE; ALLENE; CARBON; FREE RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; HEAT TREATMENT; REACTION ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

ALKADIENES; CARBON; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ENEDIYNES; FREE RADICALS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; TEMPERATURE;

EID: 53849119188 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja803413f Document Type: Article

Times cited : (66)

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- At the RBLYP/6-31G(d) level of theory, most C1-C5 cyclization diyls (e.g, 2) are not potential minima; however, the monoaryl diyls are shallow minima, and thus computational TSs (Table 1) leading from enediynes 7b-f to the C1-C5 diyls can be located by using TS search algorithms in Gaussian 03, We have used similar RBLYP calculations for the design of substrates for diradical cyclizations; see: Semmelhack, M. F, Wu, L, Pascal, R. A, Jr, Ho, D. M. J. Am. Chem. Soc. 2003, 125, 10496-10497, For the location of both the C1-C5 and C1-C6 cyclization diaryl diyls, as well as the C1-C5 TS structures (Table 2, the BS-UBLYP/6-31G(d) method recommended by Schreiner12a,c was employed. All reported DFT activation energies include ZPE corrections from frequency calculations at the same level. Activation energies obtained from BCCD
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- At the BLYP/- and B3LYP/6-31G(d) levels, E)-isomer 18 is more stable than (Z)-isomer 16 by ∼1.5 kcal/mol; thus the excess of 16 reflects a nonequilibrium mixture of products. Bu 3SnH-induced cyclization of 11 gives predominantly 18, 8b and one would expect transfer hydrogenations to do the same. Further, at the BS-UBLYP/6-31G(d) level, only the (Z)-isomer of diyl 14 is a minimum, and at the UBLYP/6-31G(d) level, only the (E, isomer of H-atom addition product 19 is a minimum although both have wide C 5-C6-Ar bond angles, To the extent that the structures of these radicals are reflected in the products' stereochemistry, the formation of less stable 16 is an indicator of diradical cyclization
- 6-Ar bond angles). To the extent that the structures of these radicals are reflected in the products' stereochemistry, the formation of less stable 16 is an indicator of diradical cyclization.

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