Evidence is provided that nucleophilic attack on five-membered ring oxocarbenium ions occurs from the inside face of the envelope. An eight-five fused-bicyclic system in which two substituents are constrained to pseudoequatorial positions underwent nucleophilic addition with selectivity that was comparable to an unconstrained monocyclic system. On the other hand, a bicyclic six-five analogue underwent reaction with low selectivity. This observation indicates that minimization of eclipsing interactions by attacking inside the envelope is not enough to control selectivity, but that the changes in the overall three-dimensional structure of the ring must be favorable as well. In the bicyclic six-five series, the six-membered ring is accommodated in the cation, but it destabilizes the transition state structure leading to the first-formed product of inside attack.

The Making Introductory Courses Real while Online (MICRO) laboratory project was developed to meet the need for hands-on experiments, focused on topics in analytical chemistry, to be delivered safely remotely or in a socially distanced in-person lab. Unlike more traditional lab experiments, MICRO laboratories use only microgram or nanogram amounts of chemicals; paper microfluidic technology is used to store and mix reactants. Instructional materials use an inquiry-based approach and are situated in a context that highlights the human impacts of the scientific analysis. To support broader-scale implementation of the experiments and promote a shift to more inquiry-based laboratory instruction, an array of supports were developed, including adaptable instructional materials, instructional videos for lab preparation, resource guides, and an introductory workshop. A cohort of nine institutions implemented MICRO laboratories both remotely and in person during Fall 2020. Students were able to successfully complete the experiments, and the inquiry nature of the laboratories led to an increased comfort with the trial-and-error nature of authentic scientific practice. Additionally, most faculty participants indicated a commitment to an increased degree of inquiry in their laboratory pedagogy.

The MICRO project has developed a series of active-learning labs that can be safely delivered to students either at home or in person using paper microfluidic technology. The skills covered in these labs are appropriate for sophomore-level analytical chemistry courses and general chemistry.

Face. -The mechanism of stereocontrol is studied in the nucleophilic substitution of oxocarbenium ions generated from bicyclic furan derivatives in which two substituents are constrained in pseudoequatorial positions (I) and (IV). The stereoselectivity achieved in the eight-five bicyclic system (I) is comparable to that achieved with the unconstrained parent furan. In contrast, the six-five bicyclic system (IV) provides a significantly lower diastereoselectivity. This results indicate that the five-membered ring undergoes a significant change of its overall three-dimensional structure. This change generates too much strain in the molecule so that the selectivity of inside attack is lost. -(SMITH, D. M.; TRAN, M. B.; WOERPEL*, K. A.; J.