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Synthesis of [60]- and [70]Fullerene-Fused Tetrahydroquinoxaline Derivatives by Oxidative [4 + 2] Cycloaddition with Unusual Reactivity and Regioselectivity

Journal Article · · Organic Letters
 [1];  [2];  [2];  [2];  [2];  [2];  [2]
  1. Rutgers University, Piscataway, NJ (United States); Rutgers University
  2. Rutgers University, Piscataway, NJ (United States)
+ Show Author Affiliations

The oxidative [4 + 2] reaction of o-phenylenediamine-derived disulfonamides with fullerene C60 and C70 is reported, in which electron-deficient reactants showed high reactivity. The reaction of C70 exhibited unusual regioselectivity, yielding a [5,6]-adduct as the major product, which was characterized by 1H, 13C NMR and single-crystal X-ray diffraction. Here, DFT calculations revealed the reaction is an inverse-electron-demand Diels–Alder (IEDDA) reaction, and the [5,6]-adduct of C70 is a kinetic product.

Research Organization:
Rutgers University, Piscataway, NJ (United States)
Sponsoring Organization:
USDOE
Grant/Contract Number:
SC0020260
OSTI ID:
2287737
Alternate ID(s):
OSTI ID: 1978215
Journal Information:
Organic Letters, Journal Name: Organic Letters Journal Issue: 35 Vol. 24; ISSN 1523-7060
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English

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Figures / Tables (6)

Scheme 1(p. 2)figure Scheme 1
Table 1(p. 2)table Table 1
Figure 1(p. 3)figure Figure 1
Scheme 2(p. 3)figure Scheme 2
Table 2(p. 4)table Table 2
Table 3(p. 4)table Table 3

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Addition reactions
Adducts
Carbon nanomaterials
Chemical reactions
Nanospheres