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Methacrolein oxide (MACRO) is an important carbonyl oxide produced in ozonolysis of isoprene, the most abundantly-emitted non-methane hydrocarbon in the atmosphere. We employed a step-scan Fourier-transform infrared spectrometer to investigate the source reaction of MACRO in laboratories. Upon UV irradiation of precursor CH 2 IC(CH 3 )CHI  (1) , the CH 2 C(CH 3 )CHI radical  (2)  was detected, confirming the fission of the allylic C‒I bond rather than the vinylic C‒I bond. Upon UV irradiation of  (1)  and O 2  near 21 Torr,  anti-trans -MACRO  (3a)  was observed to have an intense OO-stretching band near 917 cm −1 , much greater than those of  syn -CH 3 CHOO and (CH 3 ) 2 COO, supporting a stronger O‒O bond in MACRO because of resonance stabilization. At increased pressure (86‒346 Torr), both reaction adducts CH 2 C(CH 3 )CHIOO  (4)  and (CHI)C(CH 3 )CH 2 OO  (5)  radicals were observed, indicating that O 2  can add to either carbon of the delocalized propenyl radical moiety of  (2) . The yield of MACRO is significantly smaller than other carbonyl oxides.

Formation reaction mechanism and infrared spectra of anti-trans-methacrolein oxide and its associated precursor and adduct radicals