Chemists and chemical companies alike are well aware of the large amounts of waste they generate, although until recently little attention has been paid to the waste flow in terms of cost and environmental consequences. By most estimates (roughly 85%) of organic waste produced comes in the form of organic solvents. Thus, our goal continues to be the reduction of waste by focusing on organic solvents, and getting those solvents out of reactions via replacement by micellar catalysis, as quantified by E Factors.

Fluorinated compounds have blossomed in the pharmaceutical industry due to the better bioavailability through an increase in membrane permeability when compared to their non-fluorinated analogues. Micellar catalysis has been found to be amenable to radical-based trifluoromethylation of various heterocyclic compounds. Nanoreactors composed of the designer surfactant TPGS-750-M enable these substitution reactions to be performed in water at room temperature in modest to good yields in combination with Langlois’ reagent (NaSO2CF3) and t-BuOOH, negating the need for pre-functionalization. Trifluoromethylation of several heterocyclic arrays has been accomplished, including heteroaromatics.

Aromatic halogens have long served as excellent handles for transition metal catalysis and directing groups in synthesis, with subsequent need for removal. Current protocols for such dehalogenations are cost prohibitive at scale, energy intensive, and generally call for harsh reaction conditions. The new surfactant, SPGS-550-M, (‘Nok’) in water with Fu’s catalyst and a mild hydride source is used for facile debromination of aromatic compounds. These reactions take place at ambient temperatures. Furthermore, the aqueous mediums can be recycled, thus greatly reducing our dependence on organic solvents while furthering technologies in green chemistry.

Chiral compounds and their syntheses have been an intellectual curiosity of organic chemists since the first chiral resolution of tartaric acid in 1848 by Louis Pasteur. We have taken on the challenge to induce axial chirality for the natural product korupensamine D with use of an internal aromatic auxiliary blocking one face of the coupling partner via π-stacking. Korupensamine D has yet to be synthesized in its natural form, due to the inherent instability of the cis tetrahydroisoquinoline ring presenting an exciting, challenging exercise in stereo control.

Construction and maintenance of transportation systems can result in direct, indirect, cumulative, and secondary effects on ecosystems and can adversely affect the long-term viability of fish and wildlife populations (National Academy of Sciences 2005; Forman et al. 2002). Typically, mitigating adverse impacts associated with highway systems occurs on a project-by-project basis and commonly attempts to restore the same affected resource near the site where the impact occurs, regardless of regional ecological conservation priorities. This piecemeal approach may fulfill regulatory requirements but greater mitigation value may be achieved for a similar investment by evaluating and prioritizing off-site mitigation opportunities important to sustaining ecosystem processes associated with water quality, sustainable resource management practices, wildlife habitat and connectivity, and other environmental assets that contribute to a high quality of life. Further, project-by-project environmental permitting practices frequently involve repetitious procedures that sometimes unpredictably delay project delivery. Agencies want more effective mitigation approaches, while streamlining planning and permitting processes for transportation programs.

A federal multi-agency team recently developed a guide to encourage agencies to consider alternative approaches for more effective ecological mitigation and efficient transportation program delivery. The guide, entitled, “Eco-Logical: An Ecosystem Approach to Developing Infrastructure Projects” (Brown 2006; referred to as “Eco-Logical”), provides a framework and examples for agencies to collaboratively and strategically plan infrastructure projects and related mitigation to conserve and connect important habitats while increasing the predictability and transparency of infrastructure planning processes. The ecosystem approach outlined in Eco-Logical encourages expedited regulatory approvals for infrastructure projects – in compliance with applicable laws – while maintaining high standards for safety, environmental health, and effective public involvement.

Following guidance outlined in Eco-Logical, an interagency working group in Montana created the “Integrated Transportation and Ecosystem Enhancements for Montana” (ITEEM) process. As the first known effort to adaptively apply the Eco-Logical guidelines, the cooperating agencies encountered and overcame challenging issues, acquiring perspectives that may be helpful to other collaborative endeavors working to establish an Eco-Logical approach for other regions.

This report summarizes events that led to piloting the suggestions in Eco-Logical. The Eco-Logical document is briefly reviewed, followed by an account of the efforts to develop the ITEEM process using the Eco-Logical guidance, including a description of challenges encountered during the development of the process. The final ITEEM process is also described. The intent of this report is to summarize the outcomes, accomplishments and recommendations of this project for the sponsors and team members. The report also seeks to help other interagency collaborative efforts seeking alternative approaches to increase efficiency of transportation project delivery while mitigating adverse impacts where the conservation efforts are most needed.

To view or download a copy of the full report, please visit: http://www.mdt.mt.gov/research/docs/research_proj/integrated_transportation.pdf